Compendium of Organic Synthetic Methods Volume 6

Compendium of Organic Synthetic Methods Compendium of Organic Synthetic Methods Volume 6 MICHAEL B. SMITH DEPARTMENT ...

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Compendium of Organic Synthetic Methods

Compendium of Organic Synthetic Methods Volume 6 MICHAEL B. SMITH DEPARTMENT OF CHEMISTRY UNIVERSITY OF CONNECTICUT STORRS, CONNECTICUT

A Wiley-Interscience Publication

JOHN WILEY & SONS New York

0

Chichester

e

Brisbane

0

Toronto

0

Singapore

A NOTE TO THE READER

This book has been electronically reproduced from digital information stored at John Wiley & Sons, Inc. We are pleased that the use of this new technology will enable us to keep works of enduring scholarly value in print as long as there is a reasonable demand for them. The content of this book is identical to previous printings.

Copyright @ 1988 by John Wiley & Sons, Inc. All rights reserved. Published simultaneously in Canada. Reproduction or translation of any part of this work beyond that permitted by Section 107 or 108 of the 1976 United States Copyright Act without the permission of the copyright owner is unlawful. Requests for permission or further information should be addressed to the Permissions Department, John Wiley & Sons, Inc. Library of Congress Catalog Card Number: 71-162800 ISBN 0-471-84896-4 1 0 9 8 7 6 5

PREFACE It has been sixteen years since Ian and Shuyen Harrison first published the Compendium of Organic Synthetic Methods to facilitate the search for functional group transformations in the formidable body of the original literature. In Volume 2 this concept was expanded to include difunctional compounds. Louis Hegedus and Leroy Wade carried on this important compilation in Volume 3 and Wade continued with Volumes 4 and 5. Volume 6 is intended to continue the Harrisons’ stated purpose of “a comprehensive one-volume listing of synthetic methods as an intermediary between the chemist and the literature.” Compendium of Organic Synthetic Methods, Volume 6, presents the functional group transformations and difunctional compound preparations of 1983, 1984, 1985, and 1986. The classification schemes of the first five volumes have been followed but a new chapter has been added. Each literature citation now includes all authors and the text concludes with an Author Index. The new Chapter 15 classifies the oxides of nitrogen, sulfur, and selenium with section headings identical to Chapters 1-14. The difunctional compounds now appear in Chapter 16. The experienced user of the Compendium will require no special instructions for the use of the new oxides chapter or the complete volume. Author citations and the Author Index have been included to facilitate literature searches and to follow the current work of a particular author. The citations should not prove obtrusive and will hopefully assist the synthetic community . I wish to express my gratitude to Professor Michael Edwards who first suggested this project to me. I also wish to thank Professor Leon Ghosez who provided the facilities for a pleasant sabbatical leave, which allowed completion of the research for this text. My thanks to Tae Woo Kwon, Jennline Sheu, Royce Menezes, Chung Jen Wang, Paul Keusenkothen, and Young Chan Son who proofread parts of the manuscript and offered many helpful suggestions. I want to thank my wife Sarah and son Steven for their patience and moral support throughout this work.

MICHAELB. SMITH Storrs, Connecticut June 1987 V

CONTENTS ABBR EVIAT1ONS INDEX, MONOFUNCTIONAL COMPOUNDS INDEX, DIFUNCTIONAL COMPOUNDS INTRODUCTION 1 PREPARATION OF 2 PREPARATION OF AND ANHYDRIDES 3 PREPARATION OF 4 PREPARATION OF 5 PREPARATION OF 6 PREPARATION (2F 7 PREPARATION OF 8 PREPARATION OF 9 PREPARATION OF THIOETHERS 10 PREPARATION OF 11 PREPARATION OF 12 PREPARATION OF 13 PREPARATION OF 14 PREPARATION OF 15 PREPARATION OF 16 PREPARATION OF AUTHOR INDEX

ACETYLENES CARBOXYLIC ACIDS, ACID HALIDES, ALCOHOLS, PHENOLS, AND THIOLS ALDEHYDES ALKYLS, METHYLENES, AND ARYLS AMIDES AMINES ESTERS ETHERS, EPOXIDES, AND HALIDES AND SULFONATES HYDRIDES KETONES NITRILES OLEFINS OXIDES DIFUNCTIONAL COMPOUNDS

ix xiii xiv xv 1 8 19 51 67 98 113 139 164 181 194 205 239 248 272 280 493

vii

ABB R EVIAT1ONS 0 Ac acac AlBN aq.

-a

9-BBN Bn (Bz)

ii

Acetyl = -CCH, Acetylacetonate Azo-bis-isobutyronitrile Aqueous 9-Borabicyclo[3.3.1Inonylboryl 9-Borabicycio[3.3.1.]nonane Benzyl = -CH,Ph

0

I/

cat.

t-Butoxycarbonyl = -C-CB -tu 2,2'-Bipyridyl n-BUtyl = -CHzCH,CHzCH3 Carboxamidomethyl Cerric ammonium nitrate = (NH,),Ce(NO,), CycloCatalytic

CBZ COD CP CY DABCO dba DBE DBN DBU DCC DCE DDQ DEA DEAD Dibal-H Diphos-4 DMAP DME

Carbobenzoxy = -COCH,Ph 1,5-CycIooctadienyl Cyclopentadienyl Cyclohexyl 1,4-Diazabicycl0[2.2.2]octane Dibenzylidene acetone 1,2-Dibromoethane = BrCH,CH,Br 1,8-Diazabicyclo[5.4.O]undec-7-ene 1,5-Diazabicycl0[4.3.O]non-5-ene 1,3-Dicyclohexylcarbodiimide = C,H13-N=C=N-C,H13 1,2-DichIoroethane = CICH,CH,CI 2,3-Dichloro-5,6-dicyano-l,4-benzoquinone Diethylamine = HN(CH,CH,), Diethylazodicarboxylate Diisobutylaluminum hydride 1,4-bis-(DiphenyIphosphino)butane 4-Dimethylaminopyridine Dimethoxvethane

DMF

N,N-Dimethylformamide

Boc bPY WPY) Bu CAM CAN C-

0

I/

=

HCNMe,

ix

ABBREVIATIONS

X

dPPe dPPf dPPP dvb eee EE Et EDA EDTA FMN fod FP FVP hv

1,5-HD HMPA HMPT iPr LlCA LDA LTMP mcpba Me MEM MOM Ms MTM NAD NADP NBD NBS NCS PCC PDC PEG Ph Pip Pr PY quant. Red-Al TBAF TBHP

1,2-bis-DiphenyIphosphinoethane bis-(Dipheny1phosphine)ferrocene 1,3-bis-(Diphenylphospine)propane Divinylbenzene Electrolysis Enantiomeric excess Ethoxyethyl Ethyl = -CH,CH, Ethylenediamine = H,NCH,CH,NH, Ethylenediaminetetraacetic acid Flavin mononucleotide tris-(6,6,7,7,8,8,8)-Heptafluoro-2,2-dimethyl-3,5-octanedionate Cyclopentadienylbiscarbonyliron Flash vacuum pyrolysis Irradiation with light 1,5-Hexadienyl Hexamethylphosphoramide = (Me,N),P=O Hexamethylphosphorous triamide = (Me,N),P lsopropyl = -CH(CH,), Lithium cyclohexylisopropylamide Lithium diisopropylamide = LiN(iPr), Lithium 2,2,6,64etramethylpiperidide mefa-Chloroperoxybenzoic acid Methyl = - C H , p-Methoxyethoxymethyl = MeOCH,CH,OCH,Methoxymethyl = MeOCH,Methanesulfonyl = CH3SO2-Methylthiomethyl = CH3SCH2Nicotinamide adenine dinucleotide Sodium triphosphopyridine nucleotide Norbornadiene N-Bromosuccinimide N-Chlorosuccinimide Raney nickel Polymeric backbone Pyridinium chlorochromate Pyridinium dichromate Polyethylene glycol Phenyl = -C,H, PiDeridine = H&CH,CH,CH,CH,.’ . . . n-Propyl = -CH2CH2CH3 Pyridine = C,H,N Quantitative yield [(MeOCH,CH,O),AIH,]Na n-Bu,N+Ff-Butylhydroperoxide = Me,COOH

ABBREVIATIONS

TEMPO TFA TFAA Tf THF THP TMEDA TMS TMP To1 Tr TRlS Ts (Tos)

tBu

f-BUtyl = --C(CH3)3 Tetramethylpiperidinyloxyfree radical Trifluoroacetic acid = CF,COOH Trifluoroacetic anhydride = CF,COCCH, Triflate = -OSO,CF, Tetrahydrofuran Tetrahydropyran Tetramethylethylenediamine Trimethylsilyl = -Si(CH,), 2,2,6,6-Tetrarnethylpiperidine Tolyl = 4-CeHdCH3 Trityl = --CPh, Triisopropylphenylsulfonyl Tosyl = p-toluenesulfonyl

NN

Sonication

xi

I N0113310Hd I

szz

6LZ

8LZ LZZ

SLZ 61Z PLZ L LZ

ELZ SLZ

ZLZ E1Z

OLZ OLZ L9Z 602 L9Z 80Z P9Z LOZ E9Z 9OZ 092

soz

892 POZ LSZ EOZ

9SZ

ooz ESZ 661 ZSZ 861 192 L6 1 8PZ 961

9PZ S ~

SPZ €61 SPZ z6t PPZ 161 EPZ 061

IPZ 981 6EZ

P81

6EZ 181

EEZ L 081 LEZ 6L1 1EZ 8L1 EZZ ut ZZZ 9Ll OZZ SLL 61Z PLL 81Z EL1 L1Z ZLl L1Z LLL 9 LZ OL 1 S1Z 691 60Z 891 902 L91 SOZ 991

POZ sgt

EOZ E91 EOZ zgt

002 091 661 6Sl 861 8S1 861 LSL

L61 PSl S61 ESL P61 ZSL

261

ost Z61 6Pl 161 LPL 06 1 9 t1 881

stc

L81

PPl

L81

ZP1 981 OP1 S81 6El 181 8El 181 LEL

6L1 SEL SL1

PEL EL1 ZEL

1LL OEL OL1 6Z1 691 8ZL 69L LZL

891 SZ1 L91 tZ1 S91 EZL

S91 1Zl

291 ozt 191 611 091 811 8S1 LLL 8S1 911 SSL

sit

Ell

PS1 tll 6Pl

6tl Z11 8P1 111 8P1 011 9P1 601 EPL 801 opt LO1 6E1 901

sot

ZEL ZEl to1 LEL E01 8Z1 ZOL 8Z1 101 SZ1 001

SZ1 86 L11 L6 Ell

111 06

011 68 601 88 801 ~8

se

LO1

901 E8 PO1 Z8 101 18

001 6L

96 S11

S6 PI1 P6

86 LL

Ell

E6 ELL 26

89

L6 SL 18 PL 08 EL 6L ZL LL LL 1L OL 1L 69 69

69 s9 89

W

89 E9 LS Z9 L9 L9

€9 09 Z9 6s

ss

19 LS 19 9s 6S 6S

tG

86 ES 8S ZS

LS 0s 9S 6P 29 8P 1s LP

SP

SP

EP

PP

SE

zt

EE op

8E

6Z 6E 82

LZ 9E 92 SE 12

PE

02

EE 61 ZE 61 1E

91

OE

sz

91 6Z S1 82 PI LZ Pl 92 Zl

11 EZ 11

zz

01

oz

6 61

8 L1 8 91

L st 9 tl

S

zc

S 01

P 8

spunodluo3snoaueiia3siyy

SWalO

SallJJlN

sawax

(HH) S~PIJPAH

saiews 'saieuojlns 'saplieti

sapixoda 'sJaqI3

sJais3

saulluy

sap!wv

z

P

slouaqd 'sloyoqv sapwAuue 'saplieu p i x SPl3e 311AXOqJe3

SaPAWPIV

slhe 'saualAqiaw 'slAylv

Z

saualAia3v

E

1 1

SaNflOdWO3 lVNOll3NfldONOW 'XXINI

._ .-

318

305

322

340

357

341

355

354

339

351

336

351

335

371

349

368 348 370

366

347

361 344 362

343

374

387

356

385

355

381

381

354

376

351

350

361

410

362

409

400 360 401

357

392

436

367

435

366

429

365

427

453

371

452

370

448

446 369

464

374

463

373

372

458

481

481

376

375

Blanks in the table correspond to sections for which no additional examples were found in the literature.

289

311

332

340

305

331

302

288 321

329 330 332

301

309

320

327

299

317

313

296

326

325

315 316

307

292

287

285

305

282

Sections-heavy type Pages-light type

484

377

INDEX, DIFUNCTIONAL COMPOUNDS

INTRODUCTION Relationship between Volume 6 and Previous Volumes. Compendium of Organic Synthetic Methods, Volume 6 presents about 1 100 examples of published methods for the preparation of monofunctional compounds, updating the 7000 in Volumes 1 through 5. In addition, Volume 6 contains about 900 examples of preparations of difunctional compounds and various functional groups, updating the sections introduced in Volume 2. For Chapters 1 through 14 the same systems of section and chapter numbering are used as in previous volumes. Chapter 15 is new and classifies the preparation of oxides of nitrogen (nitro compounds, nitrones, N-oxides, etc.), sulfur (sulfoxides and sulfones), and selenium (selenoxides and Se dioxides) according to the scheme used for all other monofunctional compounds. Therefore, “Oxides from Acetylenes” appears as Section 21 1 and the chapter concludes with “Oxides from Miscellaneous Compounds”, Section 225. The difunctional compounds now appear in Chapter 16 (Chapter 15 in Volumes 2 through 5) but the section numbers remain the same. A minor change from previous volumes is the inclusion of thiols with all alcohol classifications and sulfides (thioethers) are classified with ethers. Both of these changes are reflected in the chapter titles, section titles, and citations. These changes do not alter the fundamental organization. Each literature citation follows the notation used in previous volumes but is accompanied by a complete author list. The principal author(s) are denoted by an asterisk (*). Following Chapter 16 is an alphabetical listing of all authors (last name, initials). Classification and Organization of Reactions Forming Monofunctional Compounds. Chemical transformations are classified according to the reacting functional group of the starting material and the functional group formed. Those reactions that give products with the same functional group form a chapter. The reactions in each chapter are further classified into sections on the basis of the functional group of the starting material. Within each section, reactions are loosely arranged in ascending order of year cited (1983-1 986), although an effort has been made to put similar reactions together when possible. Review articles are collected at the end of each appropriate section. The classification is unaffected by allylic, vinylic, or acetylenic unsaturation appearing in both starting material and product, or by increases or decreases xv

xvi

INTRODUCTION

in the length of carbon chains; for example, the reactions t-BuOH + t-BuCOOH, PhCH20H + PhCOOH, and PhCH=CHCH20H + PhCH=CHCOOH would all be considered as preparations of carboxylic acids from alcohols. Conjugate reduction and alkylation of unsaturated ketones, aldehydes, esters, acids, and nitriles have been placed in category 74 (alkyls from olefins). The terms hydrides, alkyls, and aryls classify compounds containing reacting hydrogens, alkyl groups, and aryl groups, respectively; for example, RCH2-H + RCH,COOH (carboxylic acids from hydrides), RMe + RCOOH (carboxylic acids from alkyls), RPh + RCOOH (carboxylic acids from aryls). Note the distinction between R2C0+ R2CH2(methylenes from ketones) and RCOR’ + RH (hydrides from ketones). Alkylations involving additions across double bonds are found in Section 74 (alkyls, methylenes, and aryls from olefins). The following examples illustrate the classification of some potentially confusing cases: RCH=CHCOOH + RCH=CH2 RCH=CH2 + RCH=CHCOOH ArH + ArCOOH ArH --j ArOAc RCHO + RH RCH=CHCHO + RCH=CH2 RCHO --j RCH, R&H, + RZCO RCH,COR + R,CHCOR RCH=CH2 -+ RCH,CH, RBr CH CH + RC=CR

+

ROH

+

RCOOH-,

RCH=CHCHO RCH=CHCN

+

RCOOR RCH&H&HO

+ RCH,CH,CN

Hydrides from carboxylic acids Carboxylic acids from hydrides Carboxylic acids from hydrides Esters from hydrides Hydrides from aldehydes Hydrides from aldehydes Alkyls from aldehydes Ketones from methylenes Ketones from ketones Alkyls from olefins Acetylenes from halides; also acetylenes from acetylenes Esters from alcohols; also esters from carboxylic acids Alkyls from olefins Alkyls from olefins

How to Use the Book to Locate Examples of the Preparation or Protection of Monofunctional Compounds. Examples of the preparation of one functional group from another are located via the monofunctional index on p. xiii, which lists the corresponding section and page. Thus Section 1 contains examples of the preparation of acetylenes from other acetylenes; Section 2, acetylenes from carboxylic acids; and so forth. Sections that contain examples of the reactions of a functional group are found in the horizontal rows of the index. Thus Section 1 gives examples of

INTRODUCTION

xvii

the reactions of acetylenes that form acetylenes; Section 16, reactions of acetylenes that form carboxylic acids; and Section 31, reactions of acetylenes that form alcohols. Examples of alkylation, dealkylation, homologation, isomerization, and transposition are found in Sections 1, 17, 33, and so on, lying close to a diagonal of the index. These sections correspond to such topics as the preparation of acetylenes from acetylenes; carboxylic acids from carboxylic acids; and alcohols, rhiols, and phenols from alcohols, thiols, and phenols. Alkylations that involve conjugate additions across a double bond are found in Section 74 (alkyls, methylenes, and aryls from olefins). Examples of name reactions can be found by first considering the nature of the starting material and product. The Wittig reaction, for instance is in Section 199 (olefins from aldehydes) and Section 207 (olefins from ketones). The aldol condensation can be found in the chapters on difunctional compounds in Section 324 (alcohol, thiol-aldehyde) and in Section 330 (alcohol, thiol-ketone). Examples of the protection of acetylenes, carboxylic acids, alcohols, phenols, aldehydes, amides, amines, esters, ketones, and olefins are also indexed on p. xiii. The pairs of functional groups alcohol, ester; carboxylic acid, ester; amine, amide; and carboxylic acid, amide can be interconverted by simple reactions. When a member of these groups is the desired product or starting material, the other member should, of course, also be consulted in the text. The original literature must be used to determine the generality of reactions, although this is occasionally stated in the citation. This is only done in cases where such generality is stated clearly in the original citation. A reaction given in this book for a primary aliphatic substrate may also be applicable to tertiary or aromatic compounds. This book provides very limited experimental conditions or precautions and the reader is referred to the original literature before attempting a reaction. In no instance should the citation be taken as a complete experimental procedure. Not to refer to the original literature could be hazardous. The original papers usually yield a further set of references to previous work. Subsequent publications can be found by consulting the Science Citation Index.

Classification and Organization of Reactions Forming Difunctional Compounds. This chapter considers all possible difunctional compounds formed from the groups acetylene, carboxylic acid, alcohol, thiol, aldehyde, amide, amine, ester, ether, epoxide, thioether, halide, ketone, nitrile, and olefin. Reactions that form difunctional compounds are classified into sections on the basis of the two functional groups of the product. The relative positions

xviii

INTRODUCTION

of the groups do not affect the classification. Thus preparations of 1,2aminoalcohols, 1,3-aminoalcohols, and 1,4-aminoaIcohok are included in a single section. Difunctional compounds that have an oxide as the second group are found in the monofunctional sections for the nonoxide functional group. Therefore, the nitroketone product of oxidation of a nitroalcohol is found in Section 168 (ketones from alcohols and thiols). Conversion of an oxide to another functional group is generally found in the “Miscellaneous” section, so conversion of a nitroalkane to an amine is found in Section 105 (amines from miscellaneous compounds). The following examples illustrate the application of this classification system: Difunctional Product RCEC-C~CR RCH(0H)COOH RCH=CHOMe RCHF, RCH(Br)CH,F RCH(OAc)CH,OH RCH(OH)CO,Me RCH=CHCH,CO,Me RCH=CHOAc RCH(OMe)CH,SO,CH,CH,OH

Section Title Acetyleneacetylene Carboxylic acid-alcohol Ether-olef in Halide-halide Halide-halide Alcohokster Alcohokster Ester-olefin Ester-olefin Alcohol-ether

How to Use the Book to Locate Examples of the Preparation of Difunctional Compounds. The difunctional index on p. xiv gives the section and page corresponding to each difunctional product. Thus Section 327 (alcohol, thiol-ester) contains examples of the preparation of hydroxyesters; Section 323 (alcohol, thiol-alcohol, thiol) contains examples of the preparation of diols. Some preparations of olefinic and acetylenic compounds from olefinic and acetylenic starting materials can, in principle, be classified in either the monofunctional or difunctional sections; for example, RCH=CHBr + RCH=CHCOOH, carboxylic acids from halides (Section 25, monofunctional compounds) or carboxylic acid-olefin (Section 322, difunctional compounds). In such cases both sections should be consulted. Reactions applicable to both aldehyde and ketone starting materials are in many cases illustrated by an example that uses only one of them. Many literature preparations of difunctional compounds are extensions of the methods applicable to monofunctionalcompounds. Thus the reaction RCI + ROH can be extended to the preparation of diols by using the corre-

INTRODUCTION

xix

sponding dichloro compound as a starting material. Such methods are not fully covered in the difunctional sections. The user should bear in mind that the pairs of functional groups alcohol, ester; carboxylic acids, ester; amine, amide; and carboxylic acid, amide can be interconverted by simple reactions. Compounds of the type RCH(OAc)CH,OAc (ester-ester) would thus be of interest to anyone preparing the diol RCH(OH)CH,OH (alcohol-alcohol),

Compendium of Organic Synthetic Methods, Volume 6 Edited by Michael B. Smith Copyright 0 1988 by John Wiley & Sons, Inc.

CHAPTER 1 PREPARATION OF ACETYLENES

SECTION 1 : Acetylenes frau Acetylenes 1.

2-iodothiophene Pd[PPh3I4,

HC sC-C-OH

BnEt3NC1/OH-/RT

I

CH3

2.

PhBr,

C o

CuI

80°C,

* Ph-C

50 h

Carpita, A . ; Lessi, A . ; Rossi, R.

*

80%

Synthesis, (19841, 571

[PPh3I2PdXI2 Ph-CECH

t

Ph-X

t Ph-CSC-Ph NEt3

CHC13-CuI;

X = I; X '

Bunagin, N.A.; DMF;

X = Tf;

Chen, Q-Y. Ph, Ph'

C=C=O

1.

97%

Ponomarev, A.B.; Beletskaya, I . P . M l Acad Sci USSR, (19841,

----

X'

* ; Yang, t

= Ph,

= C1,

Z-Y.

2,1171

Tetrahedron Lett, (1986), 5% Pd[PPh3I4 THF,

1433

91 %

C1

HCEC-nPr

33,

Ph2CHC

C-EPr

120°C 81 %

Mitsudo, T.; Kadokura, M.;

*

Watanabe, Y . Tetrahedron Lett, ( 1 985),

26,

3697

2

COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6

SECTION 1

2 LBu-Cl A1 C1

Me3Si-CsC-SiMe3

iH2C12,

* ; Ottana, R.;

Capozzi, G.

n B u - C =CH

Rcineo, G.; Marcuzzi, F.

Gazz Chim Ital, ---

R = Brown,

aq.

NaOH

65OC,

hv

+OoH \

8 5% Y

Brunet, J . J . ; S i d o t , C . ; Caubere, P . --J Org Chem, (19831,

9, 1919

SECTION 23: Acid Derivatives -Prom Esters

MeSiC13, Me C HC 0 Me Olah, G . A .

Y

NaI

>

Me CHC 0 H

CH3CNJ r e f 1ux

; Husain, A . ; Singh, B . P . ; Mehrota, A . K . J Org Chem, (19831, 48, 3667 ---

70%


12

0 II

e

SECTION 25

-

P t electrodes Bu4NBr,

aq.

CH3CN 94%

Kimura, M.; Matsubara, S.; Sawaki, Y. --JCS Chem Cam, (1984), 1619 0 II P hCOCH2CH =C t i 2

Te/NaBH4 EtOH,

AcOH,

2h

0 II PhCOH

*

r e f 1ux

*

Shobara, N.; Shanmugam, P.

95%

Ind J Chem B, (1986),

z, 658

Other reactions useful for the hydrolysis of esters may be found in Section 30A (Protection of Carboxylic Acids). SECTION

3: Acid

Derivatives from Ethers, Epoxides, Thioethers

and

No Additional Examples SECTION 25: Acid Derivatives from Halides c1

/

t_BuOH

CH2=C

\

c1

and SulfOMteS

+

t_BuCH2C02H

a q . H 2 S 0 4 , 2°C

* Randriamahefa, S.; Deschamps, P.; Gallo, R.

Synthesis, ( 1 985), 493

90%

SECTION 25

A C I D S FROM H A L I D E S

1 atm CO

M(CO),, PhCH

\

aq.

13

P

*

Ph-CH-C02H

Br

benzene;

R=H;

M=Fe;

n=5

*

7 5%

Tanguay, G.; Weinberger, B.; des Abbayes, H. Tetrahedron E ,(19831, EtOH/NaOH;

R=Me;

M=Co;

n=4

80%

Francalanci, F.; Gardano, A.; Foa, M. J Organomet Chem, (1985),

-

Bu4NC1 O 4 Sock, 0.; Troupel, M.;

cat. PhI

282,

277

78%

Perichon,,J. Tetrahedron Lett, (19851,

-

Pd[PPh3I4,

2, 4005

26, 1509

PPh3

e-,

Pt electrode

DMF,

E t 4 N O T s , C02

w

PhC02-Kt 92%

Torii, S.*; Tanaka, H.; Hamatani, T.; Morisaki, K.; Jutand, A . ; Pfluger, F.; Fauvarque, J.-F. C h a o Lett, (19861, 169

--


14

Q

1. LBuLi,

Br

2.

SO2,

THF,

3.

Q

-60°C

so2c1

-60°C ~

SECTION 27

--

S02C1 2/hexane

9 5%

OMe

0M e

Yonemitsu, 0.

Hanada, T.*;

Synthesis, (1986), 852

SECTION 26: Acid Derivatives from Hydrides

0”c5H11

n

COCl 2/Al C1 CH2C1

55%

Neubert, M.E.;

F i s h e l , D.L.

O r g z , (19831,

3,8

SECTION 27: Acid Derivatives from Ketones 0 II PhCCH2NEt2

1 0 30% H202 EtOH,

Wenkert,

* D. ; Eliasson,

$ \

t F u j i i , K.;

*

O°C

K.M.; R u d i s i l l , D. --JCS Chem C u m , (19831, 392

1 . HC(OMe)3,

PhC02H 8 9X

H30t

T1 ( N 0 3 ) 3 * 3 H 2 0

2. aq.

NaOH

3. aq.

HC1

Nakao, K.; Yamauchi, T.

89% t


s

SECTION 28

ACIDS F R O M NITRILES

15

1 . Z n B r 2 , MeOH, R T 2 . 1 1 5 " C , 4h

*

6

0

H

3. OH-

*

48%

4. H +

Ciordano, C. ; Castaldi, G.; Uggeri, F.; Gurzoni, F. Synthesis, ( 1985) , 436 1 . KOAc, H O C H , C H , O H

e

Me0

o

a

3 . HC1

*


1 . NaBr02/NaBr a q . NaOH, 0°C

Me2CHCH2CCH3

*

+ H30

2.

OH

80%

Castaldi, G. ; Ciordano, C.; Uggeri, F. 0 II

co

F R O M ALDEHYDES

25

nBuTi(OiPr)3, Et20

HIIIL\ CHO Ph

*

-33"- RT

P O H Ph ~ - B u

Ph *-Bu (88

12)

Reetz, M.T. * ; Steinbach, R.; Westermann, J.: Peter, R.: Wenderoth, B. Chem Ber, (1985), 118,1441

7 5%

--

(85% ee)

*

Seebach, D. ; Beck, A.K.; Roggo, S.; Wonnacott, A. -Chem Ber, (1985), 118,3673 MeTiC13,

OH

Et20

Reetz, M.T.

98%

* ; Kyung, S.H.;

Hullmann, M. Tetrahedron, (19861,

1 . PhCHO, T H F , -78"2.

% ',

PhCHCH3

2h

O'C,

/

I

>

PhCHO

9, 2931

24 h

RT

+

a q . NH4F

OH

I

PhCHCH3 78%

(85% ee)

*

Reetz, M.T. ; Kukenhohner, T.; Weinig, P.

Tetrahedmn Lett, ( 1 9861,

3, 571 1

26


SECTION 35

CuBr.Me2S Me2S, E t 2 0 , - 3 0 ° C

1 . PhLi,

n

n

b

IL6'l 3

-

60"

* (97% ee, R ) Schreiber, S.L. ; Reagan, J. Tetrahedron Lett, (1986), 2, 2945

CH3(CH2)6CH0

BnC1,

e

- ,

DMF

OH

t

CH3(CH2)6CHBn

Mg a n o d e , s t a i n l e s s s t e e l c a t h o d e , 0°C Bu4BBr S i b i l l e , S.: d'Incan, E.; Leport, L.: Perichon, J. Tetrahedron Lett, ( 1 9861,

95%

2,31 29

Review: IIReactivity and Stereochemical Factors of the Reduction of Carbonyl Functions w i t h Metallic Borohydride" Caro, B . ; Boyer, B.; Lamaty, G . ; Jaouen, G. Bull Chem Soc Fr, (19831, I1281 ---Related Methods: Alcohols from Ketones (Section 42)

SECTION 35: Alcohols ---and Thiols from Alkyl, Methylenes, and -1.3

No examples of the reaction RR' + ROH ( R ' = a l k y l , a r y l , e t c . ) occur i n the l i t e r a t u r e . For reactions of the type RH + ROH (R = alkyl or a r y l ) see Section 41 (Alcohols and Phenols from Hydri des )

.

SECTION 36

27

ALCOHOLS FROM A M I D E S

1.

PdC12, NaOAc,

CuC12 N a C l , AcOH

2. M 0 0 ~ ( a c a c ) ~

tBuOOH

*

Jitsukawa, K.; Kaneda, K.; Teranishi, S. J Org Chemj (1983)j

99%

48,

389

SiMe(NEt2)2 1 . MgBr2

I

2 . 2 MeI,

C.H,(CH " 2 )4 ,CH

THF, L i

3.

OH

I

CuI

RT

CH3(CH2)4CHCH3

6N HC1

4 . 9 0 % H 2 0 2 , DMF KHF2, 60°C * Tmao, K. ; Iwahara, T.; Kanatani, R.: Kumada, M .

Tetrahedron Lett, ( 1 984) ,

25,

67%

1909 , 1913

SECTION 36: Alcohols and Thiols from Amides -

-

M e 2 N B H 3 Na THF,

t

66"C,

'OH

6h 96X

Hutchins, R.O.*C; NEt,

Learn, K.: El-Telbany, F.; Stercho, Y P. --J Org Chem, (1984) , 9, 2438 2.2 MeLi, -78°C -RT,

8h OMe

OMe

Sibi, M.P.;

OH

THF

* Snieckus, V.

Dankwardt, J.W.: J Org Chem, ( 1 986) , 51, 271 ---

9 0%


28

SECTION 38

and Thiols from Amines SECTION 37: Alcohols ----

No Additional Examples

SECTION 38: Alcohols and Thiols from Esters

----

3 LiA1H4,

/c=N

Si02

\

C02Me

Kamitori, Y.;

CH2Ph

Et20,

Hojo,

reflux,

Cmins, D.L.

\:

CH3C

CH2

3h

.\

0.5

54%

R . ; Inoue, T.; Izumi, T. Tetrahedron E,(19831, 2,2575

LiBH4-2nBuMgC1

CH2Ph * h

THF,

r20°C,

* : Herrick,

i

CH2CHnBu

24h

I -

OH

J.J.

Tetrahedron Lett, ( 1 984), t

1. nBu4N NO3

- ( CH2) 5 C H 3

CH20H

* M . ; Masuda,

I

CH2C02Et

/ CzN

*

CH

-

1 0 % Pd-C

25, 1321

OH

I,,,,,H

benzene, 0.5h 2 . H2,

74%

~

H -( C H ~ ) 5~~ C

MeOH

6.0 %

(100% ee)

C a i n e l l i , C.: P l e s s i , L.

Manescalchi, F . ; Martelli, C.:

Panunzio, M.:

Tetrahedron E,( 1 9851,

26,

3369

SECTION 39

PhC1,

RT AcO

12h

AcO

Barton, D.H.R.

29

ALCOHOLS FROM ETHERS

* : Bridon, D.; Zard, S.Z. JCS Chem Cam, (19851, 1066 ---

35X

Related Methods: Carboxylic Acids from Esters (Section 23) Protection of Alcohols (Section 45A) Hydrolysis of Esters is covered in Section 23. SECTION 39: Alcohols ---and Thiols from Ethers, Epoxides, and Thioethers Additional examples of ether cleavages may be found in Section 45A (Protection of Alcohols and Phenols).

-&ovR

2.

R

:

HO

1. nBuLi +R /-

+ H30

Nl

1g'

0

Me

HI) +

' Y ' R Me

2)

(98

*

92%

Mikami, K.: Fujimoto, K.; Nakai, T. Tetrahedron Lett, (19831,24, 513

boMe b.. 3 Me2BBr, DCE

A

0°C + 2 5 ° C 3h

*

/k

75% * Cuindon, Y.*; Yoakim, C. ; Morton, H.E. Tetrahedron Lett, (1 983), 24, 2969

30


SECTION 39

TiC14, CH2C12 -95°C

OH

5 5%

( Z : E = 4 :1 )

Tan, T.S.; Mather, A.N.;

Procter, G . ; Davidson, A.H. 585

JCS Chem Comn, ( 1 9841, ---

OH

3 nBuLi, THF

I

- ._ t

~ J C ~ H , ~ C H P ~

B F 3 * O E t 2 , -78°C 96% E i s , M.J.;

Wrobel, J . E . ;

0

1 . mcpba, C H 2 C 1 2

C02Me

2 . Ca(OH)2, RT

4. 3 . MeOH, T F A A , 4N 0E° tC3

SMe

Young, R.N.

)t

Ganem, B. ---J Am Chem Soc, (19841,

5. NH4C1

* ; Gauthier,

Yanaguchi, M .

k

-0 C02Me

SH

97 %

Coombs, W.

J.Y.;

Tetrahedron L e t t , (1984),

nBuLi,

CH 2CH P h

106,3693

-78

25, 1753

THF:HMPA

-

0°C

t

Ph

CH2CH20H 8 2 7;

( E :Z=8 :1 )

; Hirao, I .

Tetrahedron Lett, (1984),

3,4549

SECTION 39

R = gC6Hl1; R ' = H ;

Atsunori, M.: R = 1C8H17;

31

ALCOHOLS FROM ETHERS

TiC14,

Et3SiH,

-78°C

*

Ishihara, K.: Yamamoto, H. Tetrahedron Lett, (19861, R' = H

1 . MeMgBr 2.

PCC

3 . OH-

;

.-

Vankar, Y.D.*: Arya, P.S.; Rao, C.T. R

= 1C6Hl3;

.

2.

Barton, D.H.R.*:

Syn C m u n , (19831, NaHTe/EtOH/refl ux DBE

3.

Nickel boride

1 . BrCH2CH2-CH-CH

Li

2.

90 (89% ee)

25, 3947

96%(69:31)

9, 869 75% (1OO:O)

Fekih, A . ; Lusinchi, X. Tetrahedron L e t t , (19851,

Li I

3,987

x

*

Zn/CH C1 / M e 2 S i C 1 -2 . 2 ,2

1

(96% e e l

>

Lindell, S.D.; Elliott, J.D.: Johnson, W.S. Tetrahedron L e t t , (19841,

R = "CgH19

85b

'*

26,

6197

;02Ph

HOH

Eisch, J.J.*: Dua, S.K.; Behrooz, M. -J Org Chem, ( 1 9851,

84%

2,3674

32


1 . 2Ca, EDA

0

CH3(CH213CH-CH2

Benkeser, R.A.

2 . a q . NH4C1

* ; Rappa,

A.;

91 x

Wolsieffer, L.A. them, (19861,

-J Org

1 . 2.2Ca, NH3 2h

* ; Chua,

Khoudary, K.P.:

V.: Schroeder, J . E . ; Barrans Jr., R.E.: Wang, N.: Wetzel, J . M . -J Org Chem, (1 986) , 51, 4731 CH2=CHCH2SiMe3

Oku,

51, 3391

*

2 . a q . NH4V1

Hwu, J . R .

OH I CH3(CH2)3CHCH3

*

/ \

SECTION 39

*. A . , Homoto, / \

CH2=CH-CH-CH2

TiCl 4 , CH2C1 - 8 5 " C , 5h'

Y.; Harada, T.

Ph

I

+ CH2=CHCH2C (CH2) 30H

I

Ph

quant. Chem Lett, (1986), 1495 --

M e L i / S m [ N ( T M S ) 2]3 E t 2 0 , RT, 2 3 h

Mukerji, I.; Wayda, A.

* : Dabbagh,

> CH2=CHCHCH20H 81 %

*

G.: Bertz, S.H. A r q p --Chem Int Ed (19861, 25, 760

m,

SECTION 40

33

ALCOHOLS FROM H A L I D E S

Reviews : "Cleavage of Ethers" Bhatt, M.V.;

K u l k a r n i , S.U.


"Synthetically Useful Reactions of Epoxides'l Smith, J.C.*


SECTION 40: Alcohols --and Thiols from Halides and Sulfonates 1 . MeSBCH2-

-n C 6 H 1 3 B r

*

2. o x .

"CgH13

CH 2OH

92%

Pelter, A . : Williams, L.: Wilson, J.W.: Singaram, B. Tetrahedron Lett, (1983), 3, 627, 631

I.\

1 . ( iPrO)2MeSiCH2MgC1

,'

Tamao, K .

10% c u r

* ; Ishida,

N.:

Kumada, M.

*

J Org Chem, (1983), 48, ---

91 % 2120

1 . M g , THF m

B

Me0

r

2 * [ o0' 'B-o-o-tBu THF,

overnite

3 . 2P: H C 1 ,

0°C

*M e 0 91 %

Hoffrnann, R.W.:

Ditrich, L.



34

1. nBuLi, THF,

2. 0::B-H

SECTION 40

-100°C

, THF

3 . 30% H 2 0 2 ,

1 0 % NaOH, 2 5 ° C 32%

* Danheiser, R.L. ; Savoca, A.C. Br

J Org Chem, (19851,

50, 2401

80°C

Pd[PPh3I4.

t nBu3SnCH20H,

dioxane

20h

52%

*

Sumiya, T.; Ohhashi, K.: Sano, H.: Migita, T. Chem Lett, (19851, 997 --

Kosugi, M.:

1 . [(Et3P)2Ni/NaHCNBH3]

I

( N H 2 ) 2 C = S , DMF, 6 0 ° C

2 . a q . OH3. aq. HC1

Takagi , K .

*

s

*

Chem Lett, --

t

93

x

( 1 9851, 1307

-n C 3 H 7 C H 2 C1

benzene

*

20"C, 28h

nC3H,CH2SH 65%

Molina, P. ; Alajarin, M.; Vilaplana, M.J.; Katritzky, A.R. Tetrahedron E,( 1 9851, 26, 469

t

SECTION 42A

A L C O H O L S FROM K E T O N E S

1 . H2S,

.

'TMS-C1,

2. nBuLi

Harpp, D.N.

PhCH2Br

* : Kobayashi, M.

Py

*

CH3CH,CH2CH0 3.

35

PhCH2SH

50%

Tetrahedron Lett, (19861,

3,3975

9 II

1 . NaOCH, I B u 4 N B r

n C 8 H 1 ,-C1

125"C, 1 . 5 h 2. aq.

NaOH,

Zahalka, H.A.: Sasson, Y.

*

>

nC8Hl

RT

,-OH 91%


SECTION 41: Alcohols --and Thiols from Hydrides

No Additional Examples SECTION 42: Alcohols --and Thiols from Ketones

The following reactions types are included in this section:

A. Reductions of Ketones to Alcohols. B. Alkylations of Ketones, forming Alcohols. Coupling of ketones to give diols is found in Section 323 (Alcohol - Alcohol). SECTION 42A: Reductions

of Ketones to Alcohols


36

0

Asymnetric Reduction:

!I

*

RCR'

SECTION 42A

0

1 *

RCHR'

OH R = Pr = Ph

R'

H

NH2

Ph

*

Itsuno, S. ; Ito, K.; Hirao, A.:

''

Nakahama, S.

JCS Chem C a m , (19831, 469 -J Org C h m T 1 9 8 4 ) , 9, 555

Q-

R = Me R'= Ph

(96% ee R )

30°C

, HSiHPh2

11

N

99%

*

A"'/H 2 . HOH ( 8 3 . 2 % ee R ) Ph Me Brunner, H. ; R i e p e l , G : W e i t z e r , H . &ew Chem I n t Ed Engl, (19831, 22, 331

*

R

R'

=

Me

= Bn

*

1 . HSiHPh3/[Rh(COD)C1I2 t 2 . H30

Brunner, H. ; Becker, R.: Riepel, G. Organanetallics, ( 1984 1, R

= P r

R' = Ph

S,S'

( 5 2 . 7 % ee R )

3,

I@I fOOH [PhCNH-CH-CH2-S12

LiBH4,

-

tBuOH/THF

Soai, K.*; Oyamada, H.: Yamanoi, T. R = Bu

91 %

t

1 354 98%

t

(90% ee)

JCS Chem Ccutn, (1984), 413

THF quant. ipr

32 . A NC 1 2S 0 3

/'

0L - 0

4.

Si02

L

*

Meyers, A.I. ; Himmelsbach, R.J.; Reuman, M. J Org Chem, ( 1 9831, Me0

\

pcH O 62%

48,

4053

1. LBuLi

/OMe

B rI C '"\H

2. 2Bu3B 3.

BF3*0Et2

nBuCH2CH0

+

4 . a q . HC1

Koshino, J.;

* Sugawara, T.; Yogo, T.;Suzuki, A . Syn Camnun, (1983), 13, 1149 1 . KOH,

CH3(CH ) C H N O

MeOH

>

2 . c o n c . a q . KMn04 M g S 0 4 , MeOH,

* Steliou, K. ; Poupart, M.A. Ph

CH3(CH2I6CHO 83%

0°C

J Org Chem, (19851, 50, 4971

HOCH2CH20H,

CI

6h

80°C

>

ph

SECTION 82

* T. ; Kashimura,

NaguSa, H.

S.;

A/ 68

Chem Lett, (1986),

425

SECTION 82: h i d e s from Amines

- ---

"' I

t-BU

Alper,

20 a t m CO,

H. * ; Urso, F.;

n /"\o -

Me

Ph

, 90°C PhH

t-BU

quant. Smith, D.J.H.

J Am Chem ----

Soc, (1983) ,

9,6737

1. JBuMe2SiOSO2CF3

CH2C12,

0°C

2. M e L i , T H F , P h C C l II 0 ° C - RT 0

&Ph

76%

Okazaki, R.*:

Takitoh, N.

JCS Chan Cum, ---

(19841, 192

%

SECTION 82

8

AMIDES FROM AMINES

tBuMe2SiC1

(L)

, DMF

N E t 3 , 4 O o C , 10h 4-DMAP

H

,C02Me PhCH2CH \NH2*HC1

*% Me0

Me0

Djurii, S.W.*

105

-J

N

CHO

78%

aChem, (1984), 49, 1311

n

1 . C1 3 C C H 0 , M e N U0 ,C02Me ether PhCH2CH 2 . Mg(C104)2-2HOH \ NHCHO D M F , RT 77%

*

Giesemann, G. ; Ugi, I.


- v0

4 5 atm CO ZnEt2, 100°C 18h

H

Yoshida,

* Y. ; Asano,

S.:

Inoue, S. 2 y

CH3(CH2)7NH2

co

1 8 0 ° C , P h H , 6h

CHO 80%

Chem Lett, (1984), 1073

*

CH~(CH~)~NHCHO

*

91 %

Tsuji, Y.: Ohsumi, T.: Kondo, T.; Watanabe, Y. -J Organomet (1986) , 309, 333

e,

Related Methods: h i d e s from Carboxylic Acids (Section 77) Protection of Amines (Section 105A)

106


SECTION 84

SECTION 83: Amides from Esters

---

HMPA 220"C,

m-BU

> 5h 54%

a Carmun,

Gupton, J.T.; Baran, D.; Bennett, R.: Hertel, G.R.; Idoux, J.P. 1. LDA,

(19841, 14, 7001

2 . BnNHCH2CN,

-

-70°C 3.

tL"

-7OOC

TH F- h e x a n e

Me2CHC02Et

20h

*

0

RT

a q . NH4C1

Overman, L.E. * ; Osawa, T.

THF/DMSO, NaNHTs,

66%

J Am Chem Soc, (19851,

5% Pd(PPh3)4,

*

107,

1698

TsNH2 50°C

22h

*

Bystrljrn, S.E.; Aslanian, R.: BBckvall, J.-E. Tetrahedron Lett, (1985),

SECTION ---84: Amides fran Ethers, Epoxides,

7 5%

26, 1749

and Thioethers


A M I D E S FROM H A L I D E S

SECTION 85

SECTION

85: h i d e s

CH2=C

2. CO,

1

\

CH,Br L

Mori,

and Sulfonates

f m m Halides

1. BnNH2,

Br

K2C03

NBu3,

100°C

Bn

8% Pd(OAc)2-PPh3

3. H2,

* M. ; Chiba,

K.:

Pt02

58%

Okita, M.: Kayo, I.; Ban, Y. Tetrahedron, (1985), 375

41,

1 . FleSiNEt2, DMF

Ph

3 N i ( C 0 ) 4 , 70°C 2 . HOH

Hirao, T.

107

* ; Nagata,

*

0

I1

VCNEt 85%

S.; Yamana, Y.:

Agawa, T. Tetrahedron E,(1985),

26,

5061

0 u I'I r

rn

N i ( C 0 ) 4 , 70°C

V

* T. ; Harano,

Hirao, Agawa, T.

tBuN=C=O

V

63% Y.;

Yamana, Y . ;

Hamada, Y . :

---B u l l Chem Soc Jpn, RT, 4 5 rnin 2 . Na, THF-HMPA

3. H30

Einhorn, J.;

rhiun

*

Nagata, S.:

( 1 986),

59,

PhCNH t B u

-I.

* Luche, J.L.

1341

78% Tetrahedron Lett, (1986),

3,501


108

SECTION 87

SECTION 86: -Amides from Hydrides No Additional Examples SECTION 87: Amides from Ketones

---

1 . Fp(Me2C=CH2)PF CI H 2 C H = C H 2

I

CH2CC02Me

It

0

CH2Cl

2. NH3,

6

*

CH2C12

3 . NaBH4,

MeOH

4 . CH3CN,

65OC

5. Ag20,

THF,

( -E : _Z

RT

=

2:l)

* 11% o v e r a l l Berryhill, S.R.; Price, T.: Rosenblum, M. J Org Chem, (19831, 48, 158 0 II

2 NaN3,

EtOH

reflux,

10h

NH-COEt

Br

Br

*

43%

Weber, G.: Hauptmann, S . : Wilde, H.: Mann, G. Synthesis, ( 1983), 191 1 . NH2-OS03H 9 5 % HCOOH, 2.

Olah, G.A.*;

HOH,

Fung, A.P.

pH 7,

, 3h reflux RT

Org Syn, (1984),

9,188

63%

SECTION 88

A M I D E S FROM N I T R I L E S

W?ilchli, R.; Bienz, S.:

Hesse, M. Helv Chim Acta, (19851, ---

SECTION

*

68,

484

88: hides from Nitriles 1 . LBuBr,

0

K-10 c l a y

FeN03,

EtCN

CH3CN,

*

RT

2 . HOH

w i t h 3" h a l i d e s o n l y Y Polla, E. Bull Chem Soc Belg, (19851,

----

1. LiA1(OEt)3H, PhCN

109

Et20,

35%

2, 81

0°C

2 . M e 3 S i C 1 , 0°C - RT w 3 . Me2C=C-OLi , -78 - -30°C I

4.

O"C,

I1

Et CNHtB u

OEt a q N H C1

b: 0

57%

Andreoli , P. ; Cainelli, G.!; Contento, M. : Giacomini , D.; Martelli, G.; Panunzio, M." Tetrahedron E,(19861, 3, 1695 Pip, CH3CN

2 HOH,

DMF,

160°C

sealed tube

3% RuH2(PPh3)4,

Murahashi, S.-I.

* ; Naota, T.:

24h

Saito, E.

J Am Chem Soc, ----

2

97%

(19861,

108,7846

110


SECTION 89

- --

SECTION 89: Amides fruu Olefins

NaBH4, aq.

BuNH2, NaOH

w

Barluenga, J . ; Jirngnez, C.;

v

0°C

92%

Ngjera, C.; Yus, M. I , (1 9 8 3 , 591

JCS P e r k i n ---

1 . R-NH2,

CH2C12,

Hg(NO3I2,

reflux

2 . NaBH4, BuNH2, a q . NaOH

-a

24h

0°C

-

I

R

R = C02Me

96% w

-J Heterocyclic e, (1983), 20,

Barluenga, J . ; Jirnenez, C . ; Najera, C . ; Yus, M. R = Ts

Barluenga, J.

/

1733

6 3Z w

;

Jirngnez, C . ; Nije'ra, C.: Yus, M. JCS P e r k i n I , (1984), 721 ---

C

*

Bloom, A . J . ; Fleischmann, M.; Mellor, J.M. JCS P e r k i n I , ( 1984), 2357 ---

84%

SECTION 90

111

A M I D E S FROM M I S C .

SECTION 90: Amides from Miscellaneous Compounds

--

1 . Me2C=C:

OMe

,OTMS

I

3.

Shono,

* T. ; Tsubata,

NO2 I

RMgBr,

,

TiC14

-J O r g Chem,

(19841, 49, 1056

4 A c O H , 1 % PtCl,(PPh,),, L 1 0 % SnCl,, 180°C

* Y . ; Tsuji, Y.:

7 1("

6 5%

0°C

THF,

Okinaga, N.

K.;

dioxane,

Watanabe,

OMe

J

NHAc

L

*

60 atm CO

4h

91 %

Kondo, T.; Takeuchi, R.

--J Org

9, 4451

Chem, (19841,

1. n B u L i , -78"C, THF 2. E PhCHZNPh, - 7 8 ° C

*

oC\\>\\l\jFe PPh,

3.

MeOH

4.

CAN

Broadley, K . ; Davies, S.G.

'"'P h

*

no y i e l d Tetrahedron Lett, (1984), 25°C

1 . 3 BnFIH2, 48h

2. Br2/NEt3,

*

Ojima, I. ; Kwon, H.B.

nPh

0

-Chem Lett,

-78°C

(19851,

reported

2, 1743

4f

1327

Bn

56%

112


SECTION 90

Reviews : "Synthesis and Reactions of Sulfamidesff McDermott, S.D.; Spillane, W.J. Org Prep Proc Int, (19841, llcr-Arnide Alkylation a t Carbon: Recent Advances" Zaugg, H.E.

*

Synthesis, (1984), 85, 181

5, 49


CHAPTER 7 PREPARATION OF AMINES

SECTION 91: --Amines from Acetylenes No Additional Examples

6'' SECTION

92: Amines

from Acid Derivatives

1 . NaN3, n B u 4 N B r , 0 ° C HOH/CH2C1 2 , 2h 2 . CF3COOH, CH2C12 3. K2C03/aq.

Pfister, J.R. n

U

II

CH3CHCC1

t

c1

* ; Wymann,

91 %

MeOH Synthesis, (19831, 38

W.E.

1. Pip,

PhH, NEt3

O'C,

2h

2. LiA1H4,

Et20

87 %

20h

reflux, Suzuki, K.: Okano, K . ;

*

6h

Nakai, K.: Terao, Y.: Sekiya, M . Synthesis, (19831, 723

*

SECTION 93: Amines and Thiols - frau Alcohols --

nBuOH

0 II 1 . ( E t 0 ) 2 P N H C 0 2 t B u , DEAD PPh3, 0 - 2 5 " C , 2h

2. HCl/PhH,

RT,

h u s a r s k a , E.; Zwierzak,

12h

* A.

*

+

nBuNH3 C1

-

85% Liebigs -Ann Chem, (1986), 402


114

SECTION 94

SEXTION --94: Aminea fran Aldehydes

'&

/ N TMS

OMe

Hart, D . J .

*

1.

CH2=CHCH2MgBr THF/RT,

2.

30 m i n

HOH

QMe

; Kanai , K . ; Thomas, D . G . ;

--J Org Chem,

BH3*Py, PhCHO

PhNH2,

*

Yang, T.-K.

( 1 983) ,

48,

97%

289

CH2C12 AcOH,

RT

t

PhCH2NHPh

2h

P e l t e r , A.: Rosser, R . M . ;

Mills, S.

JCS Perkin I, ( 1 9 8 4 ) , 71 7 ---

2 PhNH2, PhCHO EtOH,

Yamashita,

NaTeH

RT,

* M . : Kadokura,

93%

*

M.;

73%

Suemitsu, R .

---Bull Chem S ~ C

Jwj

1 . NH2S02NH2,

2 . MeLi, Et20

PhCHO

3 . HOH-Py

*

PhCH2NHPh

20h

( 1 984)

57,

3359

Ht

>

PhCHCH3

4 . NaOH

Davies, F.A. ; Giangiordano, M.A.; S t a r n e r , W.E. Tetrahedron Lett , ( 1986) ,

I

NH 2 95%

3,3957

AMINES FROM AMIDES

SECTION 96

115

Related Methods: Amines from Ketones (Section 102) SECTION 95: --Amines fran Alkyl, Methylenes, -and Aryls

90%

Barton, D . H . R . :

*

LeGreneur, S . ; Motherwell, W.B. Tetrahedron Lett, (19831, 24, 1601 0 1-1

-

1 . M e O C N = S = N - C 0 2 M e , 36h

2 . 2,3-sigmatropic shift 3 . L i A 1 H 4 , E t 2 0 , 4h ref1 ux

*

Kresze, G. ; Miinsterer, H.

q - P h

NH Me

43 7;

J Org Chem, (19831, 48, 3561 ---

SECTION 96: --Amines fran Amides

PhCH2CNH2

1 . P h I O , CH3CN/HOH H C 0 2 H , 1 5 h , RT 2 . H30t

>

PhCH2NH2

Radhakrishna, AJCS.; Rao, C.G.: Varma, R . K . : Singh, B.B.; Bhatnagar, S.P. Synthesis, (1983), 538

85%


116

SECTION 96

0

II

PhI(OCCF3)2, RT T H F / H O H / A g ,O 4h

t

L

Loudon, G.M. Boutin, R.H.

* ; Radhakrishna,

90%

A.S.: Almond, M.R.;

Chan,

-J

( 1 984),

H

Blodgett, J.K.;

9, 4272

38%

Zezza, C.A.;

Smith, M.B.*;

0

Ross, B.A.;

-J Org C h ,

NaBrOz, HOH

II

CH3CH2CHzCNH2

NaOH, 70°C

34%

Arhin, A . ; Cronin, P.L.E.

(19841,

*

3,4397

CH3CH2CH2NHz 73%

30 m i n

Kajigaeshi,

* S. ; Nakagawa, 1,

0

11

CH3(CH ) CN

/Me 'OMe

--

T,z-c \ /

T.: F u j i s a k i , S.

Chem Lett, (1984), 713

H

cH

/' E t O H , HC1 2. NaBH4

3. H t

Basha, F.Z.; DeBernardis, J.F.

*

M 9B r

*

0

CH3(CH2)4

N H

62%

-

Tetrahedron Lett, ( 1984),

25, 5271

SECTION 97

117

A M I N E S FROM A M I N E S Li

,

Et20,

2. LiA1H4,

Et20

1.

3L/

-t

0

Hwang, Y.C.:

4

Smith, M.B.

0

0°C

20% NaOH

3.

*

Chu, M.; Fowler, F.W. -J Org Chem, (1985), 1 . Et30+BF4-,

82%

50,

3885

CH2C1

0" C 2.

CH3N02, : 2

CH2=CHPh,

31 % Heterocycles, (1985), 3,2229

* ; 3S.h r oL fi fA, l HH%.

THF,

2d

NH C 0 2 C H 2 C h = C H 2

PPh3,

CHC13,

THF

P ~ I ~ ( d b a )H C~ O, O H ,

Minami, I.: Ohashi, Y.;

30°C

-6

Shimizu, I.; T s u j i , J.

-

*

Tetrahedron L e t t , (19851,

quant.

26, 2449

Related Methods: P r o t e c t i o n of 4mines (Section 105A)

SMZTION 97: Amines f m Amines

----

0

2 PhCH2SiMe3,

Y+

TBAF,

0-

*

24"C,

Vorbruggen, H. ; Krolikiewicz, K .

THF

>

18h

Ph

70%

-


2, 889

11 8


SECTION 97

0

0-

Webb, T.R.

5 5%

*


Chastanet, J.: Roussi, G .

*

26,

3191

J Org Chm, (19851,

50, 2910

1 . LDA

M e1 ‘0-

2. CH2=CHPh 71%

Chastanet, J.

; Roussi, G .

t

+

%Ph

(&:I=

1:0.8

%

Ph

0.3: 0.6)

Heterocycles, (1985) , 23, 653

n

0

N ‘’

Kapnang, H.

2 nPrMgBr

: Charles,

G.

*

80%


2, 1597

SECTION 97

AMINES FROH AMINES

1 . HCl/MeOH,

Et20

PhSCl , CH2C12

CH2CH =CH2

2.

C H PIH P h

3 . K2C03, N a I , C H 3 C N

I

119

> I

4. Ni(R), EtOH

Ph

51 % Ohsawa, T . ; Ihara, M . ;

Fukumoto, K . ; Kametani, T. J Org Chem, ( 1 9831, 48, 3644 ---

1 . HCO,Et,

0°C

-

reflux

L

Meyers,

4 . LDA, -100°C 5 . MeI, -100°C 6 . N H 2 N H 2 , AcOH * . I . ; Fuentes, L.M. J

0

Ph

-

hv

PIo4 MeOH

(99%ee S ) -A

105, 117

Chem Soc, (19831,

*

TMS

Lan, A . J . Y . ;

40%

Q u i l l e n , S.L.: Heuckeroth, R 0 . : Mariano. P.S. JAmChemSoc, 984), 6439 ---Yoon, U.C.; Q u i l l e n , S.L.; Mariano, P.S. Swanson, R . ; Stavinoha, J . L . ; Bay, E. J A m C h e m S o c , ( 9831, 105, 1204 ----

5

106,

*

120


SECTION 97

opC O O H NaBH4, THF 12h

OMe OMe

Ymada, K . ;

Takeda, M . ;

Iwakuma, T.

*

68% (60% ee)

JCS Perkin I, (1983), 265

5 % [PdCl 2 - C u C 1 2-NaC1 CH2=CH(CH2),NH2

Pugin, B. ; Venanzi,

6.5h

* 2 Am L.M. Ti02,

-

*

HCl] 60"C,

Me Me0

7 5%

Chem Soc, (1983),

P t , HOH

105,6877

*

R T , hv

H

*

Nishirnoto, S.; Ohtani, B.; Yoshikawa, T.: Kagiya, T. J Am Chem Soc, (19831, 105, 7180 ----

1 . n C H Br, C H C 1 3 , - 3 7

60°C

-

c

I

Me

2 . NaSPh, 2 - b u t a n o n e CH3CN,

I

r e f l u x , 24h

_?.C3H7 7 0%

Manoharan, T.S. ; Madyastha, K.M.*; Singh, B.B. ; Bhatnagar, S.P.; Weiss, U . Synthesis, ( 1983) , 809 Ind J Chem B, (1984), 23, 5 ----

SECTION 97

121

AMINES FROM AMINES

0 Y

0

LBuOK

1. x - B u L i , O"C,

lh

I

2 . nC8H17Br, 1 6 h

Me

-

-78°C

RT

*

Ahlbrecht, H. ; Dollinger, H. Tetrahedron Lett, (1984), 1 . BF3/THF,2 0 2 4 h , RT

70%

25, 1353

0

2 . NaOH/HOH 93%

Mora;es, H.R.*; Pdrez-Juirez, M.: Cueha, L.; Mendoza, L.: Fernandez, H.; Contreras, R . @ Ccamun, (1984), 2, 1213

9 Me

0 II

1 . C1COCHCH3 , D C E I c1 0°C

-

reflux

2 . MeOH, 5 0 ° C

-

*

-9

NH* HCI

reflux

97%

Olofson, R.A. ; Martz, J.T.; Senet, J.-P.*; Piteau, M.: Malfroot , T. --J Org Chem, (1984), 9, 2081

n

HO

NH

Bn

Sammes, P.G.

1 . A g B F 4 , MeOH

2 . HBF4/THF

* ; Smith,

t

Bn 51 %

S.

--JCS Perkin I, (1984), 2415

122

SECTION 97


1. tBuLi, 2.

THF,

-25°C

HMPA, C B u B r

*

I “\t - 1 3 ~

Meyers, A.I.

3.

NH2NH2

* : Edwards,

Meyers, A . I . * ;

Bn

N / \

Me/ ‘0-

Tokitoh, N . ;

W.F.; z,

Rieker,

I

*

1. tBuSiMe20Tf, MeLi,

THF

3 . BnC1,

10h

4.

THF

TBAF,

Okazaki,

Tokitoh, N.:

CH2C1

*

I,) I

Bn

58%

* R. ; Suzuki,

He*;Manabe, H. Chem Lett, (1984), 1937

--

2. MeLi, 3.

74%

H.: Maruoka, K . ; Yamamoto, H. Tetrahedron Lett, (1984), 25, 2367

1. tBuSiMe20Tf,

Me/ ‘0-

Bn

10h

O’C,

2.

B a i l e y , T.R.

t

C H 2‘C 1

OC02Et

0

u

JAm Chem (1984), 106,3270 P.D. : m e y , T.R.: Jagdmann Jr., G . E . --J Org Chem, ( 1 9851, 50, 1019

4 Me3A1

F u j i w a r a , J . ; Sano,

B

53%

P.D.:

Edwards,

?

H-

0

PhMgBr

Okazaki, R.

*

THF

CH2C1 t

I

Bn 74%


25, 4677

SECTION 97

123

A E I N E S F R O M AMINES

RT

1 . FeC12, H O H , 2h

/ 'B n

H

2 . E D A , PlaOH, P e t e t h e r

-0

67%


Monkovic, I . ; Wong, H . ; Bachand, C . 1 . NCS,

2OoC

0 . 1 Torr )c 2 . H02C(CH2)4C02H

C H CH CH N H

20° C, 0 . 1 T o r r

Guillemin, J . C . ;

Denis, J.M.

r-7 Y

B F3 2.

Me

E i s , M.J.

aq.

: Ganem,

B.

Synthesis, (19851, 1131

* O Et 2

t

94%


NaHTe

Barton, D.H.R.

nBuCH2CH2NHMe

t

NH~OH

E t O H , RT

Ph

85%

THF

1 . "Bu,CuLi, L

t

H C H ~ C H ~ C H ~ N ( c1

*

26,

W N H Ph

pH 6 - 7 t

1153

quant,

; Fekih, A . : Lusinchi, X . Tetrahedron E,( 1 9851,

2, 3693

124


SECTION 97

-

e , graphite e l ec t r o d e

H

2.5h,

LiBr

20% a q .

Elof son, R.M. ; Gadallah, F.F.

: Laidler,

Can J ---

J.K. Chem, (19851,

[#L 1 . TiC13,

-78OC

Hb

71%

CH3CN

a\

63, 1170

THF

-

RT

~

2 . a q . NaOH

Murahashi,

* S. ; Kodera,

Y.

83%

Tetrahedron

E ,(19851, 26,

4633

1 . LDA, chexane - 7 8 O C

-

RT,

18h

H

2 . HOH

Pearson, W.H.

* ; Waters,

6' OEt

*

Haga, K . ; Iwaya, K.: Haga, K .

*;

63%

M.A. ; Oswell, K.D.

J Am Chem ---O#O,

Soc, (1986),

12h

c a t . pTsOH, r e f 1ux

PhCH3

-Ph iiiti

(1)

.

Ph ( 5 1 )

108,2769

-0 y Ph,

0 Et

90%

Kaneko, R. Bull Chem Soc Oohashi, M . ; Kaneko, R. B u l l Chem Soc

---*,(19861, 59, 803 ---*,(1984), 57, 1586

125

A M I N E S FROM HALIDES

SECTION 100

Review: "Nucleophil i c Additions t o Tet rahydropyridinium S a l t s : Applications t o A 1 k a l o i d Syntheses"

Stevens, R.V.

*

Accts Chem Res, (1984),

17, 289

SECTION 98: Amines frau Esters Pip H O C H C H = C H C H OAc

THF,

(El Gene^, J . P .

20°C

H O C H C H = C H C H 2-h

(L)

cat. P ~ ( P P ~ ~ ) ~

* ; Balabane,

lh

3 6 5%

BBckvall, J.E.*: Nystrijm, J.E. Tetrahedron @, ( 1 9831, 2, 2745

M.;

CH 2=CHCH 2 0 A ~ Pd(PPh3)4

NEt3, T H F , 2 5 O C

H B e r g b r e i t e r , D.E.

* ; Chen,

----

B.

84%

JCS Chem Carm, (1983), 1238

SECTION 99: Amines fran Ethers, Epoxides,

and Thioethers


Nishiyama, K.*:

Tanaka, N.

JCS Chem Ccnm, (1983), 1322

126 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6

6

1 . Mg, THF

50%

*

Takahashi, T.:

Sekiya, M. JCS Chem Cam, (19841, 794

---

1 . M g , Et,OL

Br I

0

2. (Ph0)2P-N3 #'

-

Et20, -72°C 3. HOH Mori, S.;

6"'

t

2.[Me3Si12NCH20Me 3. MeOH

Morimoto, T.;

SECTION 100

Aoyama, T.; S h i o i r i , T.

*

+

RT

89%

-


gR

25, 429

ref1 u x

H

R R

Me

8 = LBu ( 92 *9 5 % Tetrahedron E,(1983), Hrubiec, R.T.; Smith, M.B. =

(

91 %

HMPA, 15OOC

*

24h

.

Y

GUDtOn. J.T. J U ~ .C, .D ;

* J . P . : Baker,

: Idoux, Rampi, R.c.

92 ) 8 ) 2,5031

76% C.;

-J Org Chem,

Colon, C.:

(19831,

48,

Crews, A.D.; 2933

AMINES F R O M H A L I D E S

SECTION 100 Br

-n B u 3 S n N E t 2 ,

NEt,

PhCH3

*

PdCl 2 ( g T o l 3P)2 100°C, Kosugi, M.;

Kameyama, M.;

3h

61 %

M i g i t a , T.

PhBr,

*

Chem Lett, (1983), 927

10% Pd(PPh3I4

3 KOH, cBu4NBr

QBEt2

THF,

*

reflux, Ih

I s h i kura, M. ; Kamada, M. ; Termhima, M.

85%

*

Heterocycles, ( 1 984),

22,

265

EN..

,C’

1 . Me3SiCH2NMe2

Nakano, M . ;

127

acetone t 2 . C s F (KI), H M P A R T ; 206 7 4% Sato, Y. JCS Chem C m , (1985), 1684

*

---

Me0

PhCH3, l h

7 6% Malmberg, H . ; N i ls s on, M.

Review:

*

Tetrahedron, (1986),

2, 3981

Y opper A s s i s t e d Nucleophilic S u b s t i t u t i o n of Aryl Halogen”

Lin dl ey, J.

*

Tetrahedron, (19841,

40,

1433


SECTION 102

SECl'ION 101 : Amines fran Hydrides

--

1. nBuLi, 2.

TsN3,

Et20,

3. i c e 4.

RT,

Et20,

KOH/Ni(Al),

24h

0°C

0

-

25°C 80%

Narasirnhan, N.S.; Ammanamanchi, R.

Tetrahedron L e t t , (1983), 24, 4733

Q"

CN

NH3,

hv,

a q . CH3CN

88%

*

z,

Yasuda, M . ; Yamashita, T.: Matsumoto, T.; Shima, K.: Pac, C . --J Org Chem, ( 1 9851, 3667

b

SECTION --102: Amines fran Ketones N-0 Ms

1. Me3SiOTf 2.

Sakane, S.; Maruoka, K . :

*

Dibal-H

Yamamoto, H.

*

*

3


87%

24, 943

129

A M I N E S FROM KETONES

SECTION 102

5 Dibal-H CCH3(CH2)4]2C=NOH

0-20°C

*

[ C H 3 (CH2 I 4 l 2 N H

85%

*

Sasatani, S.; Miyazaki, T.: Maruoka, K . ; Yamamoto, H. Tetrahedron Lett, (19831, 24, 4711

L

II

CH3 ( C H 2

N O M ~

-

1 . Et2A1C1 i+

2.

Dibal-H

CH3(CH2I1

0 H

53%

Sakane, S . ; Matspura, Y.; Yamamura, Y.; Ishida, Y.: Muruoka, K . ; Yamamoto, H. J Am Chem Soc, (1983), 105, 672 ----

& :

Ac OH

nBu3P

v

OAC

N

'OH

6

Barton, D.H.R.:

0

A b e , K.;

C7H15

'Y H NHz

NaBH3CN

PhSSPh TH F

94%

'Y'

Ac OH

CN NHz 'good y i e l d '

Na CN

Motherwell, W.B.; Simon, E.S.; Zard, S.Z. --JCS Chem Cam, (1984), 337 1 . NaBH3CN,

NaBr

MeOH,

4d

2 . pH 3 , 3.

RT,

RT, 3h

+

HO Me

pH 1 1

Okmura, H.: Tsugoshi, T.; Nakamura, N. Synthesis, (19841, 597

H 80%

*

H C 7 H 15


N N Me,

1 . E B u L i , THF,

-78OC

2.

-78°C

P h S C u , THF,

SECTION 102

0 II

3. CH2=CHCCH3, 4. H30

* ; Liu,

Kelly, T.R.

t

82%

_--J Am

H.

Chan Soc, (1985),

1 . NaN3,

y 3

-70°C

55OC,

BrCH2CH2CHCCH3

107, 4998

DMSO

18h

I1

0 Vadtier,

M.:

* 65% RT, 1 2 h Lambert, P.H.: Carri;, R. Bull Chem Soc Fr, (1986), I1083 ----

H*r.F H 3

p""" \

1 . LiA1H4,

THF

NHZ

t

2. HOH

HIlkPh Me 73%

(44% ee R )

I t s u n o , S.*: NBn

Me,

Me'l

II

C-C-CH3

CH2C1 Sulmon, P.:

Tanaka, K . ; 1.

Ito, K.

-Chem Lett,

2 L B u O K , THF reflux,

2 . H30

De K i m p e , N .

2h

t

* : Schamp,

* N.

JCS Chem Carm, ---

(1986), 1133

JNH I

(1986), 1677

Related Methods: Amines from Aldehydes (Section 94)

95%

SECTION 103

AMINES F R O M NITRILES

131

SECTION 103: Amines Prom Nitriles

--

1 . 3 LiA1H4, T H F reflux, 15 min CN

New,

CN

2 . H30

* J.S. ; Yevich,

t

NH,

62% Synthesis, (19831, 388

J.P.

1 . Dibal-H, -70°C

-

PhCH3 RT

>

2 . NaF, O ’ C , 3 0 m i n I 85% 3 . H O H , 0°C - RT * Overman, L.E. : B u r k , R.M. Tetrahedron Lett, (1984), 25, 5737 HSiMej,

CO

2

b

c a t . Co2 ( C O ) 8 P h C H 3 , - 2 0 - -60°C

,Ivi) 61 %

Murai, T.*; Sakane, T.; Kato, S. Tetrahedron Lett, (19851, 26, 5145

6

Weiberth, F.J.:

-

1 . iPrMgC1, T H F

r e f l u x , 2h 2. LiNH2,

PhC02Na

*

“5 60%

Hall, S.S.

)c

J Org Chem, (19861, ---

2,5338


SECTION

SECTION 105

104: Amines fran Olefins

aq. NaHC03, 10°C 3 . 10% H C 1 4. 3 N N a O H Kabalka, G.W.

* ; McCollm,

-J Org Chem, C.W.:

60%

Kunda, S.A.

(19841,

2, 1656

Review: "Amination of Alkenes" Casc,

M.B.; Lattes, A.:

Perie, J.J.

Tetrahedron, ( 1 9831,

2,703

SECTION --105: Amines from Miscellaneous Compounds 1. nBuLi

CH3Li.NHMeOMe Kokko, B.J.;

Beak,

* P.

t

2. H O H

CH N HnBu 72%

Tetrahedron

G,(19831, 24, 561

1 . ( o t 3 C H , 1 1 O°C 4h

&02

Lloyd, D.H.:

2. T i C 1 3 Nichols, D . E .

H

*

62% Tetrahedron Lett, (19831,

2, 4561

AMINES F R O M M I S C .

SECTION 105

Ph

1 . L D A , THF,

Nco

-nC3 H7 B r ,

''',Po

-

3.

-78OC 3h

*

EtOH,

2 . NaBH4, 80°C,

133

35h

70% H2S04,

18h

H

""0 94%

(98% ee)

* (1983), 9, 7754

Guerrier, L.: Royer, J.; Grierson, D.S.: iiusson, H.-P.

_--J Am

1 . SnC12,

CN

CI

Bellamy,

~

Vaultier, M.; R z l l C g H 13

Soc,

2HOH,

EtOH

7OoC, 3 0 m i n 2.

* F.D. ; Ou,

0-

C-

5% a q .

*

NaHC03

1 . P P h 3 , THF, 2. HOH, 12h

Knouzi, N.:

*

95%

1 2 h )-.

Carrie, R.

Tetrahedron

4 HC02NH4, Pd/C,

NaTeH,

*

96%

Tetrahedron Lett, (1984), 25, 839

K.

E ,( 19831, 24, 763 MeOH

-+

Gartiser, T.; Selve, C . ; Delpeuch, J.-J. R = Bn

CI

CN

Tetrahedron L e t t , ( 1 9831,

EtOH/Et,O,

Suzuki, H. ; Takaoka, K .

RT

Chem L e t t , (19841, 1733

93%

24, 81 %

1609


1 . BC13,

PhH

*

10 m i n

2. H30

Zanirato, P.

*

t

H

JCS Chem Cam, -,-

1. tBuLi,

2.

(1983), 1065

THF,

-78°C

-

RT,

3h

?Q

3 . 3 N: lH 2: N2 H 29 ,5 % pEHt O 8H,: A c1 O5 Hh :

L N. '

91%

I(CH2)4C1 -78OC

.Me

S E C T I O N 105

OMe

61%

t -Bu

Meyers, A.I.

* : Marra,

26, 5863

Tetrahedron E,(1985),

J.M.

t

Me2N=CH2 C 1 PhSnMe3

CH2C12,

24h

w

PhCH2NMe2

r e f 1 ux

Cooper, M.S.: N02

I

Heaney,

,

OH

CH 3 C C H 2 C H 2 C H C H

I

* H.

1 . NiC12.6H20 N a B H 4 , MeOH 2.

CH3

Osby, J.O.

: Ganem,


* B.

Dowex-50(Ht) NH3/MeOH

65%

3, 5011

,

NH2

*

OH

I

CH 3CCH CH CH CH

I

CH3

-


7 6%

26,

6413

SECTION 105

R-

AMINES FROM M I S C .

9-

NapTe/aq.

*

Suzuki, H. ; Manabe, H.:

R-

Ph

NaOH/dioxane/50°C

Inouye, M.

1.

iBu2Te

2.

TiC14/CH2C12

:

~

O

H

Boldrini , G . P .

R-

Chem Lett, (1985), 1671

3 . HOH

Me3Bn,

R

2. aq.

*

74%

-

HFe(C0)4-

HC1

3.

Na2C03

; Cainelli , G . ; Urnani-Ronchi,

-J Organomet Chem,

Q

95%

t

Chem Lett, (19861, 549

H a n a z a k i , Y.

Suzuki, H.*;

135

80%

* A.

(1983)

2113,

1 . [ H g C l ? / T H F / M g , RT] t 2 . T i C 1 4 , L B u O H , 0°C HO * Syn Coaarm, (1983), George, J.; Chandrasekaran, S.

R = -CH2CH2CHMe2

HC03NH4, MeOH,

Ram, S.:

Ehrenkaufer, R.E.* EtOH/HOH, ASO, Y.;

Watanabe, Y .

-

40 m i n

*

Tetrahedron=, 80°C

PhH

94%

13,495 82%

(19841,

3, 3415

-+

72%

*

O t s u b o , T.: Ogura, F. Chem Lett, (1984), 853

Rz O O M e

R = QNO2

RT,

[PhTeTePh/NaBH4],

Rz Ph

Ohira, N.:

1 O%Pd/C

195

* : Ohta,

--

RuC12(PPh3)3,

NEt

T.;

HCOOH

*

, E t OH,i%?CTv5F--T s u j i , Y.;

97%

Hiyoshi, T.; T s u j i , Y .

Bull Chem Soc s,(19841, 57, 2440 --P t C 1 2 ( P P h 3 ) 2 , SnC14 NEt3, a q . d i o x a n e , CO * quant.

RT Watanabe, Y .*: T s u j i , Y.; O h s u m i , T.; Takeuchi, R. Bull Chem Soc (19841,

--- s,

57, 2867

136 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6 SECTION 105A

600 p s i H2,

@=

polystyrene Baralt, E.; Holy, N.

SECI'ION

=:

EtOAc,

* --J Org Chem,

100°C

(19841,

80%

2, 2626

Protection of Amines

Related Methods: Amides from Amines (Section 82) Amines from Amides (Section 96) /NH-BoC 1.

Kim,

NEt3

9

*

iP r C H

\

COOH

2. Ht

0

* S. ; Chang,

i P r C H , ,NH 2 COOH

H.

--JCS Chem Carm, (19831,

98%

1357

c1 I

BOC-OCHCC13,

PhCH2NH2

20"C,

Barcelo, G.;

H

Kim,

* S. ; Lee,

+

PhCH2NHBOC

s a t d . K2C03

S ene t, J.-P.;

0

THF

Sennyey,

* G.

-J Org Chem,

O S B O C CH2C12,

RT, 1 5 m i n

J.I.; Y i , K.Y.

91 %

50,

*o

( 1 9851,

3951

0 t - Bu 95%

--will Chem Soc s,(19851, 58,

3570

SECTION 105A

Kapnang, H.; Charles, G .

6

137

PROTECTION OF AMINES

Ph3CSC1,

*

Tetrahedron

aq.

THF,

E, (1983), 24,

Na2C03

--+

3233

NHSC Ph,

96%

1 . T M S - I , CH,Cl,, L +--- . 2. aq. EtOH

Branchaud, B.P.

*

Me2Si\

L

-78°C

-.-

-.-

_-

TRS g r o u p

J Org Chem, (1983),

,CH LI

La

IY I'I

CH -

e

1'1

-

e

g, 3538

Zn12

2'S,iMe2,

I*

(trityl sulfenyl)

92%

/ /

LI

IY

140°C

si

\..'Si

\

9 2 7

2 MeOH,

Guggenheim, T.L.

PhCH2NH2

*

c a t . pTsOH quant.

-

Tetrahedron Lett, ( 1 984),

( T M S ) 2~~~

3, 1253 0

*

PhCH2NHCOCH =CH2

C1 F,0CH=CH2

Raucher,

0 * S. ; Jones,

D.S.

II

97%

Syn Cornnun, (19851,

3,1025


1 . BOC20, 2. PhCH2CH2NHAc

MeCN

Et2NCH2CH2NH2 MeOH,

3.

DMAP,

PhCH2CH2NHBOC

94%

l h

NH2NH2/MeOH,

Grehn, L.; Cunnarsson, K.:

t

3d

Ragnarsson, U .

JCS Chem Cam, (1985), 1317 ---

nii

1 . PhCH=CHCH20COR HOH, N E t 3 , DMF

y 3 NH2CHCOOH

HOOCCH2,

t

NH I

c=o

2 . H,O+

I

I

P hCH =CHCH

Kinoshita, H.*; Inomata, K.: Kameda, T.: Kotake, H. Chem L e t t , (19851, 515

/"

9 5%

--

P~CH~CH~NHCBZ CH2C12,

King, P.F.

* ; Stroud,

Overman,

Tetrahedron

S.G.

,

NEt3,

MeCN

92%

RT

U

+

83%

PhSitBuCl

1" only

2h

RT,

U

25°C

7 4%

M.E.; Mishra, P. Tetrahedron Lett, (1986), 27, 4391


CHAPTER 8 PREPARATION OF ESTERS

--

SECTION 106: Esters from Acetylenes

nB u C=C C H

P d C 1 2 , C u C 1 2 , HC1 O2

1 a t m C O Y MeOH R T , 2h

nB u

*

H

* Alper, H. ; Despeyroux, B.;

Woell, J.B. Tetrahedron Lett, (19831,

1.

nBuC=C- I

1-J+h2~~

Hoshi, M.; Masuda, Y.: Arase, A.

/

‘c = c \

C02Me

72%

3, 5691 0

2. Z B u S M g B r , -50°C

HMPT 3. H 2 0 2 , N a O H

/CH 3

- \

*

*

I1 nB uCH CS n B u 83%

JCS Chem C a m , (1985), 714

SECTION 107: --Esters from Acid Derivatives

The following types of reactions are found in this section: 1. Esters from the reaction of Alcohols with Carboxylic acids,

Acid Halides, and Anhydrides.

2. Lactones from Hydroxy Acids.

3. Esters from Carboxylic Acids and Halides, Sulfoxides, and Miscellaneous compounds.


SECTION

0::: 0

br

1. 2 PhP(TMS)2 CH3CN, 4 h , -15°C

C02Me

2. 4 MeOH,

C02Me

24h ref1 u x

62%

*

Appel, R . ; Htlnerbein, J.: Knoch, F. Angew Chem Int Ed Eslgl,

(19831,22, 61

0

0

I1

ClCOBn, NEt3, 0°C C H ~ ( C H ~ ) ~ C O O H c a t . DMAP, C H 2 C 1 2 Kim,

* S. ; Lee,

30 m i n

97%

J . I . : K i m , Y.C. J Org Chem, (1985), 50, 560

-

1. nBu3SnStBu,

PhCH2SC1

RT,

* ; Aida,

@="1 Amos, R . A .

P h C H SS t B u

90%

Tetrahedron Lett, (1 9831, 2,51 73

-

@P P h 2 0 C H 2 0 H

(f)

0

II

Et20

T.; Chan, T.H.

PhCH=CHCOOH

24, 3365

CHC13

3 min

2 . a q . KF, Harpp, D.N.

II

CH3(CH2)6COBn

Tetrahedron Lett, (l%3),

011

107

THF, DEAD,

25°C

PhCH=CHC02Bn

(L)

86%

ystyryl

; Emblidge, R.W.: Havens, N . --J Org Chem, (1983), 48, 3598

SECTION 107

ESTERS FROM A C I D S

c,',"O

e - x y l ene,

Mukaiyama, T.

* : Ichikawa, J.:

r e f 1ux

* Widmer, U.

HN- CH 2CH P h

86%

Asami, M.

(tBuO)2CHNMe2, PhCH3,

Go

.*

PhCH2CH2NH2, 3 h

H

141

Chem Lett, (19831, 683

80°C

30 m i n

* 82%

Synthesis, ( 1 983 1 , 1 35 nPrOH,

PhCOOH

RT

Py,

30 m i n

N '

*

*

PhCOCH2CH2CH3

o z N O N O ~ CI

94%

Takimoto, S. ; Abe, N.; Kodera, 'Y.; Ohta, H. Bull Chem Soc (19831,

A%

Ph

kOOH

--- s,

cone. H 2 S 0 4 20"C,

72h

*

56,

639

Ph

84% Sychkova, L.D.; Kharitonova, O.V.; Shabarov, Yu.S. J Org Chem USSR, (19831,

2, 1298


Mandal,

* A.K.

lh ---Ind J Chem B, (1983), 22, 505

H? CHCH2CH=CH(CH2)7COOH I

llCgH1 3

(L)

Cais, H.-J.

*

SECTION 107

88%

1 . Me2NCrCC02Me 2 . CH2C12, 40°C

*&o

cat. camphor sulfonic acid

0 82%

Tetrahedron Lett, (19841, 25, 273

/-w < c 0

T M S O ( CH2), 4 C 0 2 T M S

nPr2BOTf PhCH3, ref1 ux 8h

>

(

* K. : Kotake,

Taniguchi, N.; Kinoshita, H.: Inmata, Chem Lett, (19841, 1347

--

CH~(CH~)~COOH

*

Kim, S. ; Lee, J.I.:

BnOH, CH2C12 RT, 2h KO, Y.K.

0

*

H.

94%

CH3(CH2)6C02Bn 94%


ESTERS F R O H ALCOHOLS

SECTION 108

e CH3CH2CH2COOH

-,

EtI,

143

P t electrodes

Et4NOTs, RT

CH3CH2CH2C02Et

DMF

96%

*

Nonaka, T. : Fuchigami, T. -Chem Lett, (1985), 371

Awata, T.; Baizer, M.M.;

Further examples of the reaction RCOOH + ROH + RCOOR are included i n Section 108 (Esters from Alcohols and Phenols) and Section 10A (Protection of Carboxylic Acids). SECTION 108: Esters from Alcohols -and Thiols

- --

0

b

II

0

OCPh

II

&H

3 PhCOTf,

CH2C12

py,

- RT

-78°C

81%

Brown, L.: Koreeda, M.

is.

*

--Ja C h e m i i i ,

8 Br2

5 Ni(OBz)2

OH

20°C

*

Doyle, M.P. ; DOW, R.L.:

9,3875 (1983), 1113

J Org Chem, (19841,

>

d-

0

0

+

99%

Bagheri, V.: Patrie, W.J. J Org Chem, (1 983), 48, 476


SECTION 108

84%

* Kageyama, T. ; Kawahara, S.; Kitamura, K.: Chem Lett, --

Ueno, Y.; Okawara, M. (1983), 1097

NaBr03-HBr

*

HO(CH2)40H CC14,

5h,

37°C

78%

*

Kajigaeshi, S. ; Nakagawa, T.; Nazasaki, N.; Yamasaki, H.: Fujisaki, S. Bull Chem Soc Jpn, (1986), 2,747 ----

f o H

RhH( P P h 3 I 4

\

? OH

PhH,

50"C,

10h

t

t 82%

*

*

Ishii, Y.; Suzuki, K.; Ikariya, T.; Saburi, M. ; Yoshikawa, S. J Org Chem, (19861, 5l* 2822 * Ishii, Y.; Osakada, K.; IEariya, T.; Saburi, M. : Yoshikawa, S. -J Org Chem, (1986), 2,2034

,

CH20H

(CH2)8 CH20H

'

(bipy)H2CrOC1

N O

C'

>

\

/

CH2C12, R T

*

Chakraborty, T .K.; Bhushan, V.; Chandrasekaran S . Ind J Chem B, (1983), 22, 9 ----

2

0

ESTERS F R O M A L C O H O L S

SECTION 108

0

t

I1

0

1 . Me2N=CHOCPh, E t 2 0 2 0 ° C , overnight

CH3CH2CHCH20H

145

II

+

CH CH C H C H 2 0 C H

*I

2 . d i l . a q . H2S04

* Barluenga, J. ; Camps,

CH3 65%

P.J.; Gonzalez-NGez, C.; Asensio, G. Synthesis, ( 1 985) , 426

CO, THF, C H 2 = C H C H 2 C H 20H

C u C l 2,

22

PdC12

HC1

RT

*

0

overnight

6”

*

Alper, H. ; Leonard, D.

JCS Chem Comn, (1985), 511

+(i C02E t

C O Y C O ~ ( C O ) ~E , t O H 900 p s i , 1 9 0 ° C HOH, 24h

CI

(jH

60%

* Shim, S.C.; Antebi, S.; Alper, H.

CI

68%

6

--J Org Chem, (19851, 9, 147 0

5cch3 II

0 I1

CH3CSH,

Zn12

CH2C12,

30 m i n

\

0 Me

?4

Gauthier, J.Y. ; Bourdon, F.: Young, R.N. Tetrahedron E ,(1986), 3, 15

85%


HLADH = H o r s e L i v e r A l c o h o l

Lok, K.P.;

Dehydrogenase

* Jakovac, I.J.: Jones, J.B. J Am Chem Soc, ----

SECTION 109

(97% ee)

(19851,107,2521

Further examples of the reaction ROH + R'COOR are included in Section 107 (Esters from Carboxylic Acids and Acid Halides) and Section 45A (Protection of Alcohols and Phenols). SECTION 109: -Esters from Aldehydes LiW02,

2 0 PhCHO

75"C,

0

THF

II

t

72h

PhCOBn 89%

* J.S.

Villacorta, G.M.; Filippo Jr., --J Org Chem, (19831,118, 1151

Me \Nx

'j

N

M

nBuC-H I E t

Y.J.; Ahn, K . H .

Tetrahedron Lett, (1983), 24, 3369 95%

Syn Cornnun, --

J.S.

i

Et20,

* S. ; Hong,

PhCH 2 S C H 2 B r

C.Y.;

PhCH2Ph 99%

Yang, S.

hgew Chem Int Ed Engl, ( 1 983),

'gH14'

M.

t

0.2h

C O ~ ( C O ) ~A1, 2 0 3

* : Gopal,

3,603

(19851,

Zn(BH4)

PhCHPh

Alper, H.

Et20

M = Sn

* S. ; KO,

0 II

MC12],

96%

Br

Kim,

JCS Chem Cam, (1983), 907

M = Zn

* S. ; K i m ,

X = Br,

quant.

RT

2.5h,

E t

0Me

h..

"3"

* ; Goh,

[ 2 NaBH3CN,

Et

SECTION 160

RT, 2h

22,

0

I!

*

PhCH2SCH3 quant.

-

J Org Chem, (1983), 48, 4390

562

HYDRIDES F R O M HALIDES

SECTION 160

201

Br

Osuka, A . :

PhCCHCH3

78%

Chem Lett, (19831, 119

Suzuki, H.

1 . SnC12, 2 Dibal-H TMEDA, THF, PhCH3

I

-78"C,

Br

6

2 . pH 7

Oriyama, T.; Mukaiyama, T.

\

Boyer,

10 min

0

*

PhCCH2CH3

+

Chem Lett, (19841, 2069

NaH2P02, T H F , 65°C Na2C03, c a t . P d - C

* S.K. ; Bach,

II

81 %

\

HOH

96%

J . ; McKenna, J.; Jagdmann J r . , E.

-J Org Chem,

( 1 9851,

50,

3408

Br

NiC12, H O H ,

HMPA, Yamashita,

* J. ; Inoue,

NaI

60°C

o),>))

t

91 %

Y.; Kondo, T.; Hashimoto, H. wlll Chem Soc *,(19851, 58, 2709

---


tBuOOJBu, hw,

DMF,

NaBH4 80°C

SECTION 162

>

6h

74%

Abeywickrema, A.N.; Beckwith, A.L.J.

-


cat. PhCCH2Br

3, 109

P d ( P P h 3 ) 4 , 160°C

PMHS,

*

CH3CN/DMS0

Bn3N, 3h

PhCCH3 8 0%

PMHS = p o l y m e t h y l h y d r o s i l o x a n e

Pri-Bar, I.*; Buchman, 0.

OTf

J Org Chem, (19861,

51,

734

2% Pd(OAc)2, N E t 3 4% PPh3,

6OoC, l h

Cacchi, S.; Ciattini, P.G.; Morera, E.;

* Ortar, G.

-

Tetrahedron Lett, ( 1 9861,

91 %

3, 5541

SECTION 161 : Hydrides from Hydrides

No Additional Examples SECTION 162: Hydrides from Ketones

This section lists examples of the reaction R,CCOR

+

R,C-H.

SECTION 164

H Y D R I D E S FROM N I T R I L E S

203

5 CF3COOH, H O H b

reflux,

15h 93%

36

Keumi, T. ; Morita, T.; Inui, Y.; Teshima, N.; Kitajima, H. Synthesis, ( 1985), 979 SECTION 3: Hydrides from Nitriles

-8

This section lists examples of the reaction RCN 1 , K, PhCH3 18-crown-6 &N

-*

RH.

d i cR yT c l o h e x a n e 2 . HOH

*

95%

Ohaawa, T. ; Kobayashi, T.; Mizuguchi, Y.; Saitoh, T.: Oishi, T. Tetrahedron E, (1985), 26, 6103 SECTION 164: Hydrides from Olefins


204


SECTION 165

SECTION 165: Hydrides from Miscellaneous Compounds

"10"2!

H

./

Oda, H.;

c =c

/

\

H

nBu4NF

S iMe2Ph

H M P A , 80°C 30 min

b

"1

OH21 >=cH2 CH3

77%

*

Sato, M.: Morizawa, Y.; Oshima, K. ; Nozaki, H. Tetrahedron Lett, (1 983), 24, 2877

NaHTe, RT,

EtOH

1 5 rnin

*

85%

Suzuki, H. ; Takaoka, K.; Osuka, A. W 1 Chem Soc .7pn, (19851, 58, 1067

---


CHAPTER 12 PREPARATION OF KETONES

SECTION 166: Ketones from Acetylenes 1. HSiMe(OEt)2 2 . H2PtC1 6 * 6 H 2 0 RT,

nBuC=CnBu

30 m i n

3 . 30% H202, KHCOQ

*

nBuCH2CnBu 82%

r e f 1 ux

t.:eOH/THF,

*

0

It

Tarnao, K. ; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics, ( 1 983 1,

2, 1694 0

1 . HgC12, K2C03 BnOCH2CnCH

THF,

t

RT

2 . H30+

*

6 0%

Barluenga, J. ; Aznar, F.; Liz, R. 1.

Q Ph'

nB u C s C H

* Yamashita, A.

95OC,


C=Cr (CO)

DWF, 1 2 5 " C , 2.

II

BnOCH2CCH3

15h

5h

>

WBU 0

95%

Tetrahedron E,(19861,

3, 5915


SECTION 167

SECTION 167: Ketones fnw Acid Derivatives

-

35%

*

Tetrahedron

Chou, T.-S. ; Huang, S.-B.

PhMgX, THF

CH3CH2CH2COOH

e, (19831, 24, 2169 0

It CH3CH2CH2CPh

*

Ni ( d p p e ) C l

65%

r e f 1 ux

Fiandanese, V.; 0

II

PhCCl

Marchese, G.*; Ronzini, L. Tetrahedron E ,(1983), PhCH2C1 , g l y m e , 8 5 O C

Inaba, S.: Rieke, R.D. 0

0

+

*

J Org Chm, (1985),

-

PhCH2CPh

25'C,

6h

5% P d ( P P h 3 ) 4

2,1373

73%

OYPh

C l e Z n C l , THF

PhCCl

11

45 min

Nio,

II

2, 3677

-+ CI -.

* Negishi, E. : Bagheri, V.;

J . A . ; S t o l l , A.T.

95%

Chatterjee, S.; Luo, F.-T.; Miller,

Tetrahedron

w, (19831, 24, 5181

SECTION 167

K E T O N E S FROM A C I D S

1 . iPr2Zn, Et20, 0-23°C BnPdCl ( PPh3)2

nC3H7CC1

Grey, R.A.

0

2. 3 N H C 1 , 1 6 O C

PhCCl

0 II -n C 3 H7 C i P r

t

98%

J Org Chem, (19841, 49, 2288

CH3CH2CH21,

I1

207

Zn-Cu

Pd(PPh3)4 PhH -DM F

cat.

0 It

*

PhCCH2CH2CH3

*

Tamaru, Y.; Ochiai, H.; Sanda, F.; Yoshida, Z. Tetrahedron L e t t , (1 9851,

-

0

1 . C p 2 T i = C H 2 , -20

It

PhCH2CC1

2. H C 1 ( s ) ,

Stille, J . R . :

Grubbs, R.H.

- 1 0°C

*

-

3°C

26, 5529 0

>

I1

PhCH2CCH3

J: Am Chem Soc, (1983),

97%

9, 1664

n

3. a q . HC1

*

85%

Fujisawa, T. ; Mori, T.: Higuchi, K.; Sato, T. Chem Lett, (1983), 1791

--

I

77%

Me


CU20/O2

*

Ph2CHCOOH CH3CN,

50"C,

PhCPh

15h

57%

Toussaint, 0 . ; Capdevielle, P.; Maumy, M. Tetrahedron E,(19841, C02SiMe3

1

CH2

I

C02S iMe3

Rathke, M.W.

CH20Ac

I

(CH2)4

I

c-c1

br

1 . MgC12, N E t 3 , E t 2 0 2 . PhCC1, O ' C , l h II 0 3.

* ; Nowak,

SECTION 167

5N HC1,

0

II

PhCCH

>

reflux

Syn

M.A.

25, 3819

90%

Camnun, (1985),

3,1039

1 . EBuMnI, E t 2 0 -50°C

-

RT

2 . a q . HC1 , 0°C

CH20Ac

i

*

( CI H 2 ) 4 0

2h

95%

Friour, G . : Cahiez, G.*; Normant, J . F .

E t 3 A 1 , THF,


25°C

PhCCl

Wakamatsu, K . ; Okuda, Y.;

Oshima,

&""B" -

* K. ; Nozaki,

*

0

II

PhCEt 70%

H.

Bull Chem Soc *,(1 9851, 58, ---

2425

SECTION 168

0

K E T O N E S F R O M ALCOHOLS

1. nC7H15MgBr,

II

THF,

RT

N i ( d p p e ) C1

PhSCCl

2. IBuMgBr, THF,

209

*

Fe(acac)3 0°C

E C ~ H5 C~ ~ B u

84%

Cardellicchio, C.; Fiandanese, V.: Marchese, G.*: Ronzini, L. Tetrahedron Lett, ( 1 985), 26, 3595 SECTION 168: Ketones from Alcohols and Thiols \OH

1. Cr(C0)6 2. Ac20/Py

t 3 . CH-CHMeOTMS, L

Reetz, M.T.

ZnCl I2

,

4. * ; Sauerwald, M.

Q&OH

[

A

H+

22°C

67%

CH2C1

Tetrahedron E,(19831, 24, 2837

12Cr207

-2

bo

-

A

95% * Lopez, C.; Gonzalez, A.; Cossio, F.P.; Palomo, C. -Syn Conmun, (19851, 15, 1197

0 OH

CH2C1 2 - C C 1 2 CH3C03H,

* Corey, E.J. ; Barrette, E.P.;

4 y

0°C

30 min

*

Magriotis, P . A . Tetrahedron E,(1985),

96%

26, 5855


SECTION 168

P

4 [ HN-NL J H]'CrO3C1 CH2C12, 7h Davis, H.B.:

Sheets, R.M.;

G.L.

*

82%

Brannfors, J.M.; Paudler, W.W.;

Card,

Heterocycles, ( 1983) , 20, 2029

BU

5% P d ( O A c ) 2 6% PPh3, NaH, T H F

P h B r , 50°C

Bu

*

80%

Tamaru, Y.: Yamada, Y.; Inoue, K . ; Yamamoto, Y.; Yoshida, Z. J Org Chem, (19831, 48, 1286 ---

b

Choudary,

Pd(OAc)2/NaHC03 PhI, Bu4NC1 , DMF RTj 48h

* B.M. ; Reddy,

-6 95%

N.P.; Kantam, M.L.: Jamil, Z. Tetrahedron L e t t , (19851, 26, 6257

-

OH (NH4)6M07024'2H20 I C H ~ C H ( C H ~ ) ~ C H ~ OTHH F , 7 d , R T 30% H 2 0 2 , K 2 C 0 3 Bu4NC1

*

*

Trost, B.M. ; Masuyama, Y .

0

II CH3C(CH2)8CH20H


7 9%

3,173

SECTION 168

KETONES FROM ALCOHOLS

Et H OCH 2 C H C H ~ P ~

3 LBuOOH, PhH

I

OH

21 1

E t

*

8 O o C , 24h

HOCH2bHCnPr II0

97% Kaneda, K.; Kawanishi, Y.; Jitsukawa, K.; Teranishi, S. Tetrahedron Lett, ( 1 9831, 24, 5009 Mo(CO)~, cetylPy.HC1 MgS04, 4 h 96%

* : Ogawa, M.

Yamawaki, K.; Yoshida, T.; Suda, T.; Ishii, Y. Synthesis, ( 1986 1 , 59 P M O 2~ 0 4 0 ~ - 3 c e t y l p y 3

7 85 hO C

quant. * * Yamawaki, K.; Yoshida, T.: Nishihara, H.; Ishii, Y. : Ogawa, M. -Syn Cornnun, (1986), 16, 537

6

NaBr02, a q . AcOH RT,

Kageyama, T.;

* Ueno, Y. ; Okawara, M.

OH

AcOH, C O ( O A C ) ~

1

CH3(CH2)4CHCH3

8

-t

30 m i n

84%

Synthesis, (1983), 815 0

li

*

CH3(CH2)4CCH3 67% * Morirnoto, T. ; Hirano, M.; Wachi, M.; Murakami, T. --JCS Perkin 11, (19831, 1949 N a B r , 60°C, l h

BaMn04, PhH r e f l u x , 15h

&OH

*

Firouzabadi, H. ; Mostafavipoor, Z.

*

$0

90%

Bull Chem Soc Jpn, (19831, 56, 914 ----


OH

I

CH2=CHCHCH3

5% t r a n s Mo ( N 2 ) ( d p e l

SECTION 168

0

II

CH3CCH2CH3

-P

PhH, reflux, l h

95%

Tatsumi, T.: Hashimoto, K.: Tominaga, H.; Mizuta, Y.; Hata, K . ; Hidai, M.: Uchida, Y. -J Organomet Chem, ( 1 9831, 252, 105

-

1 . BF3*OEt2, DCC

CH,Cl,,

RT, lh

2. P h I O , 0 ° C - R T 4h ~~

0

II

7

PhC( CH2)3CH=CH2 81 %

*

Ochiai, M.; Ukita, T.; Nagao, Y.: Fujita, E. JCS Chem Cam, ( 1 9841, 1007

---

0

II

1 . C1 C O C H 2 C H = C H 2 2 . Pd(OAc)2,

8 0 " C , 2h

Tsuji,

OH

I

* J. ; Minami,

PhCHCH3

CH3CN

t

I.; Shimizu, I. Tetrahedron Lett, ( 1 9841,

-

Pt-Ti02, PhH hv,

15h

*

t

7 6%

25, 2791 PhCCH3 83%

Kussein, F.H.; Pattenden, G. ; Rudham, R.: Russell, J.J. Tetrahedron Lett, ( 1 9841, 25, 3363

-

SECTION 168

+

OH

I

F R O M ALCOHOLS

KETONES

-

B nNMe O M o B r

t B u O O H , THF

CH3( C H 2 ) 6 C H ( CH2)30H

21 3

60"C,

C H 3 (CH2) gC(CH2)30H

24h

* Masuyama, Y. ; Takahashi, M.;

0

II

60%

Kurusu, Y. Tetrahedron Lett, ( 1 9841,

c e t y l NMe3 CH2C12,

-

t

Mn04

25, 441 7

-

30°C

1 .5h

OH

*

90%

Rathore, R.; Bhushan, V.; Chandrasekaran, S. -Chem Lett, (19841, 2131

OH

I

C H 3 (CH ) 5 C H C H

0 RuC13(H20),/NaBr03 A1 i q u a t 3 3 6 ,

C H C l 3/HOH,

RT

*

I1

CH3(CH2)5CCH3 82%

4.5h

*

*

Yamamoto, Y.; Suzuki, H. ; Moro-Oka, Y. Tetrahedron Lett, (1 9851,

26,

OH

I

PhCHPh

21 07 0

3 Ag2Fe04, reflux,

PhH

0.8h

>

I1

PhCPh 97%

Firouzabadi, H.: Mohajer, D.; Moghaddam, M.E. Syn Coamun, (1986), 16, 211

21 4 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6

SECTION 168

0

OH

I

Kanemoto, S.; Tomioka, H.;

I1

*

CAN

CH3 ( CH2)7CHnPr

CH3(CH2)7Cn-Pr

* Oshima, K. ; Nozaki, H.

Bull Chem Soc Jpn, ----

(19861,

9 4%

2, 105

Ba F e 0 4 PhH,

reflux 24h

*

80%

Firouzabadi, H. ; Mohajer, D.; Enterzari-Moghaddam, M.

-Syn C m u n ,

OH

PhH,

I

C H ~ C (HC H ~5 ) ~

~

Ni(R),

( 1 9861,

reflux

3 Dean S t a r k t r a p

*

3h

*

Krafft, M.E. ; Zorc, B.

16,723

J Org Chem, (19861,

CH3C(CH2)5CH3 93%

2, 5482

Review: ?Thromiun ( V I ) Based Oxidants”

*

Firouzabadi, H. ; IranpOor, N.; Kiaeezadeh, F.: Toofan, J. Tetrahedron, (1986), 3, 719 Related Methods: Aldehydes from Alcohols and Phenols (Section 481

SECTION 169

KETOP!ES FROM ALDEHYDES

SIXTION 169: Ketones

CHO

I

Ph-C-CH2CH=CH2

from Aldehydes

[ R h ( c h ir a p h o s ) 2 ] C 1

I

; Young, C.G.

JCS Chem Corrm, ---

1 . C 1 C 0 2 E t , NaCN, R T Bu4NC1, C H 2 C 1 CHO c 2 . NaH/DME, c l a l

RT, 1 .5h 3 . M e I , 0°C - RT

* Au, A.T.

Q

Syn Corrmun, --

(19841,

2,743,

*

749

0

Q

P P h

I

*

Ph

2 . KOH/MeOH

Anders, E. ; Gassner, T.

76%

Chem Ber, --

1 . EBuMgBr, VC13 CH2C1 2 , PhCH3

*

\

50%

I1

QJCHO

c'K 0

1 . PhCOC=PPh3

*

Cfh

(19831, 1215

0

CHO

50%

(52% ee S ) 3S-bis-(diphenylphosphino) butane

i

James, B.R.

*

160°C, 10h

CH3 c h i r a p h o s = 2S,

21 5

2 . CH2C12, r e f l u x

Hirao, T. ; Misu, D.: Agawa, T.

J Am Chem ----

(1984),

117,1034

*

Soc, (19851,

66%

107, 7179

0

216 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6 /

V

NO

N

y NH' 0

CH3CH0

M~o-K+,K ~ C O ~

*

SECTION 170

* 72%

Kirmse, W. ; Hellwig, G.; Van Chiem, P.

Chem Ber, (1986), --

119, 1511

-

SECTION 170: Ketones fran Alkyls, Methylenes, and Aryls

This section lists examples of the reaction R-CH,-R' R-c ( =o)-R'

3 . CH2CHkC1,

Q

3

Beswick, P . J . ;

0

Muzart , J.

0

THF, 2 h -78°C- RT

3

62%

Leach, S.J.; Masters, N.F.; Widdowson, D.A. JCS Chem Coam, (19841, 46

---

RuC13,

NaI04, 21h

CH3CN,

RT,

CH2Cl 2/CC1

*

pH 7

Hasegawa, T.; Niwa, H.; Yamada, K.*

PhCH2Ph

+

62% P O Chem Lett, (19851, 1385 *

*

, O O C , 8h

0

II

I1

PhCPh 87% (46% conversion) Tetrahedron Lett, ( 1 986), 27, 31 39

-

-

SECTION 172

KETONES FROM A Y I N E S

21 7

SEXTION 171: Ketones from Amides

-

--

Me

Comins, D.L.

* ; Brown,

8 5%

J.D.

Tetrahedron Lett, (19831, 2, 5465 0

1 . P h L i , THF, O ° C

*

lh

2 . H30

t

I1

PhCCH3 77%

Wattanasin, S . ; Kathawala, F.G. Tetrahedron Lett, (1984), 25, 811

-

SECTION 172: Ketones -from Amines

6

1 . C1C02Me 2 . MeOH, E t 4 N O T s , e 3 . MeOH, 5 % H2S04

Me0 OMe

* 69%

*

Shono, T. ; Matsumura, Y.; Kashimura, S. -J Org Chem, (1983), 18, 3338


SECTION 173

SECTION 173: Ketones from Esters

0

II

0

nBu2CuLi, E t 2 0

CH3(CH2)6CSeMe

-78OC,

w

I1

CH3(CH2)6C~Bu

15 min

96%

Sviridov, A.F.: Ermolenko, M.S.: Yashunsky, D.V.; Kochetkov, N.K. Tetrahedron E ,(19831, -n ritlu - 2

* Kim, S.

Lee, J . I .

c

LUL ’ ’i ,

(1983), 48, 2608

I1

d

1 . LiCH(rJC5Hl,)P(OEt)2 RT

3. (COC1)2, DMSO,

NEt3

CH2C1 2 , -6OOC 4 . !aH,

THF,

* &

“CgH1

-78OC

2 . NH4C1, H O H ,

I!

nBuC( C H 2 ) 5 B r

90%

0

THF,

4355, 4359 0

Et20 t

JOrg Chm,

24,

1

27%

RT

Attenbach, H.-J. ; Holzapfel, W.; Smeret, C.: Finkler, S.H.

26, 6329

Tetrahedron Lett , (1 9851,

P hC O-N=C

fH3 1 . CH3CH2CHMgBr

QN

\

C H 2 C 12 ’ T H F y Ph

2 . HOH

* Miyasaka, T. ; Monobe, H.:

Noguchi, S.

0 OoC

I1

PhCyHCH2CH3 CH3 72%

-Chem Lett,

(19861, 449

21 9

KETONES FROM ETHERS

SECTION 174

0

1 . Me3SnCH2-,

I1 PhCOCH2CH3

-78OC,

0

THF

It

3h

PhCCH3

-t

2 . a q . NH4C1

*

Sato, T. ; Matsuoka, H.;

84% Igarashi, T.: Murayarna, E. Tetrahedron L e t t , (1986), 3, 4339

-

SECTION 174: Ketones -from Ethers, Epoxides, and Thioethers

-

0

CH3

I

/ \

Me2C-CH(CH2)2fH Bn0CH2CH2

5% L i c 1 0 4 ,

CH2C1 2 / T H F ,

OSiMe3

I

I1

Me2CHC(CH ) CH

91 %

2l

*

B nOCH 2 C H

K.; Torii, S. Tetrahedron Lett, ( 1 9831, Fujii,

Cr03,

PhCHPh

RT

P t e l ec t r o d e s

Uneyama, K.: Isimura, A.;

0

e-

H2S04

acetone

2,2857 0

II

t

PhCPh

82%

*

Baker, R . ; Rao, V.B. ; Ravenscroft, P.D.; Swain, C . J . Synthesis, (19831, 572

0

II S-C H C P h I

1.

hw,

PhH

2 . MeO-N-OSiMe2tBu

*

II

CHMe

3 . TBAF,

Vedejs,

* E. ; Perry,

D.A.

THF

J Org Chem, ---

86%

(1984),

2, 573


220

0

Bn

3 NaSePh

0

"

PhS,

/ \

/

C-CHMe

RT,

SECTION 175

t

20 m i n

92% Izawa, T.; Sakata, K.;

Satoh, T . ; Kpeko, Y.; Yamakawa, K .

Kumagawa, T.;

Satoh, T.: Kaneko, Y . ;

Izawa, T.; Sakata, K . ; Yamakawa, K. --wlll Chem SocJp~,(1985), 58, 1983

0

/ \

nC8H1 , C H - C H 2

Chem Lett, --

(1984), 1957

0

S m I O , THF RT,

I1

*

20h

nC8H, 7 C C H 3 85%

SmIO = 2 S m 1 2 t 1 / 2 O 2

Prandi, J.: Namy, J.L.:

*

*

Menoret, G.; Kagan, H.B. J Organmet Chem, (19851, -

285,

449

SECTION 175: Ketones from Halides and Sulfonates

-

PhI, CO, CH3CH2CH21

Tarnaru, Y.;

Zn-Cu,

-

0

Pd(PPh3)4

THF,

50°C,

I1

Id)

PhCCH 2 C H 2 C H

(75% conversion) Ochiai, H . ; Yamada, Y.: Yoshida, Z.

-

*

90%


1 . Mg,

3. EtfiI20,

0

Friour, G.; Alexakis, A.:

0

THF

II

THF:PhH

*

82% t

Cahiez, G. ; Normant, J . Tetrahedron, ( 1 984), 40, 683

SECTION 175

AgOCCF3, 60°C,

* Ishihara, T. ; Kudaka,

PhCH2Br Tanguay,

221

KETONES FROM H A L I D E S

T.;

MeOH

20h

6 6%

T.

Ando,


Fe(C0I5,

2OoC

Ca(OHI2,

HOH

*

0

I1

BnCBn

+

BnCOOH

78%

CH2C12, 3h G.; Weinberger,

22%

* B . ; Des A b b a y e s , H . Tetrahedron Lett, (1 984), 3,5529

0 I

Ph3A1,

DMSO,

1 % PdC12(MeCN)2,

GPh

>

4OoC 4h

\

OMe

OMe

Bumagin, N.A.;

* I.P.

Ponomaryov, A.B.; Beletskaya, Tetrahedron Lett, (19851,

-

1 . Mg,

EteO

2. VC13,

nBuBr

Hirao,

25, 4765

-78OC,

* T. ; Misu,

3.

&I

CH2C12 20 min

,

-78x-RT

D.; Yao, K.; Agawa, T.

-

98%

2,4819

Meo


86%

3, 929


SECTION 176

C O ~ ( C O ) ~M , e1 a q . NaOH, CO,

*

20°C,

PhH 20h

Me3Ncetyl Br

Miura, M. ; Akase, F.; Nomura, M. 1. Ac20,

DMF,

e-,

JCS Chem Ccm, (1986), 241 Mg a n o d e

s t . steel cathode

PhCH2C1

2.

Bu4NI, 10°C aq. H2S04

d'Incan, E.: Sibille, S.;

2 0%

54%

Perichon, J. Tetrahedron=,

0

It

PhCH2CCH3

80%

(19861,3, 4175

Related Methods: Ketones from Ketones (Section 177) Aldehydes from halides (Section 55) SECTION 176: Ketones from Hydrides

This section lists examples of the replacement of hydrogen by ketonic groups, RH + RCOR'. For the oxidation of methylenes, R,CO, see section 170 (Ketones from Alkyls and R,CH, Methylenes). -+

Bestmann, H.J

.* ; Schobert, R .

2,791

Angew Chan Int Ed Engl, (19851,

K E T O N E S FROM KETONES

SECTION 177

223

Ketones

SECTION 177: Ketones

This section contains alkylations of ketones and protected ketones, ketone transpositions and annelations, ring expansions and ring openings, and dimerizations. Conjugate reductions and Michael alkylations of enones are listed in Section 74 (Alkyls from Olefins. For the preparation of enamines or imines from ketones see

Section 356 (Amine - Olefin).

Me

65OC

63%

*

Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett, (1 9831, 2, 3865 CO,Et

1 . TiC13,

DME,

2. NEt3, 3. DME,

*

-

LiA1H4 10 min reflux,

reflux,

1 .5h 24h

4 . a q . MeOH

McMurry, J.E. ; Miller, D.D.

Go

M e A l C1

82%

J Am Chem Soc, (19831, 105, 1660

t

CH2C12 25OC,

0

3h

(9

')

85%

Snider, B.B.** Cartaya-Marin, C.P. J Org C h m , (19841, 49, 153 J Am Chm-SGE (19831, 105,2764 Snider, B.B.*i Kirk, T.C. ----


1 . IBuMgBr,

0

II

2.

CICH~CCH~C1

-20

-

Li,

-20

SECTION 177

MgBr2

2OoC,

-

4.5h

0

*

2 0 0 ~

II

CH3CH2CcBu

3 . a q . HC1

Barluenga,

180°C, 2h * J. ; Florez, J.: Yus,

2 5%

4.

* ; Hahn,

Molander, G.A.

0

II

PhCCH2Br

quant,

J Org Chem, (1986),

G.

1. LiN(TMS)2,

2.

TMS-C1,

THF,

-78OC

3. 2 CBuLi, 4. aq.


M.

-

-78OC RT

-78OC

PhCCH2CH3

II

t

PhCCH2SiMe3 51 %

*

Wierner, D.F. -J Org Chem, (19861,

II

0

NH4C1

Sampson, P.; Hammond, G.B.;

0

51, 1135

51, 4342

1 . K H , THF, t B u M e 2 S i C 1 / N E t 3 2 . t B u L i - T M E D A , nC6H14,

-1

ooc

3. ~ B u 1 ,-5"C,

45 m i n

*

0

II

P h C C H C H 2nBu

4 . HOH

*

62%

Trirnitsis. G. : Beers, S.: High, J.: B r u t t s , D.

Ridella, J.; Carlon, M.;

--JCS Chem Carm, (1984),

Cullin, D . ;

1088

SECTION 177

KETONES F R O M KETONES

225

-6 0

0

0

I

1'

CH3CCH2

NH3,

Galli, C.: Bunnett, J . F .

-

, FeS04

DMSO,

*

1 0 min

60%

J Org Chm, (19841,

d

*

P h C H 3 , Mn(OAc)7 AcOH, r e f l u x

CH3CCH3

3,3041

51%

CH,

( 2 : m : ~= 6 8 : 2 0 : 1 2 )

Cardrat, C.

Bull Chem Soc Belg, (1984),

NMe2

II CH3CH2CH2CCH2CH3

Fe(N0)3 C H 2 C 1 2, r e f 1 u x

78 %

*

Ph'fi'p,

0 II CH3CH2CH2CCH2CH3

K-10 c l a y

Laszlo, P. ; Polla, E.

n

93, 897


K-10 c l a y , F e ( N 0 ) 3

CH2C12,

2.5h,

RT

*

3, 3309

Ph

98 %

Balogh, M . ; Cornelis, A,*;

Laszlo, P.

#

Tetrahedron=,

(1984),

25, 3313


* Olah, G.A. ; Arvanaghi, M.;

SECTION 177

88%

Ohannesian, L.; Prakash, G.K.S.

Synthesis, (1 9841, 785

S

II

nBu4N

PhCPh

t

HS04-, C H 2 C 1 2

3N NaOH, R T , l h

0

I1

w

PhCPh 90%

Alper, H.: Kwiatkowska, C.; Petrignani, J . - F . ; Sibtain, F. Tetrahedron Lett, (1986), 7, 5449 K-10 c l a y , C H 2 C 1 2

S

Ph!QN02

0

*

Ph1'oN02

F e ( N 0 3 ) 3 , R T , 30 min

94%

Chalais, S.:

* Cornelis, A.; Laszlo, P. ; Mathy, A . Tetrahedron Lett, (19851, 26, 2327

0

II

CH 3CCH 2 C O O H

Kjonaas, R.A.*;

0

1 . C B u L i , T H F , 0°C 2 . B n B r , T H F , 3d O°C - R T

Patel, D.D.

w

II

CH3CCH2CH2Ph 92%

-

-


SECTION 177

b

2 27

KETONES FROM KETONES

DMF, N E t 3

1 . Me3SiC1,

reflux, 17h 2 . EtC(Me)2C1 , TiC14 C H 2 C I 2 , -5"C, 2 . 5 h

* 38%

Reetz, M.T.*; Chatzoosifidis, I.: Hubner, F.; Heimbach, H. OrgSlm_, (1984), 62, 95 /X

Q

K-10 c l a y , F e ( N 0 3 ) 3 CH.2C1 2

0 I1 X = NHCNH2,

7 0- 90%

N H S 0 2 T o l , NhPh

*

Laszlo, P. ; Polla, E.

q

Fe\+''

Ph,P

/


1 . "BuLi,

.co

)f 0

-Q

-7SOC

2 . TFlSCl 3. n B u L i , THF, - 7 8 ° C 4 . CH20, THF 5 . MeLi, - 7 8 ° C

w

6 . Me1

Davies, S.C. 0

77%

* : Walker, J.C.

--JCS Chem C m

, (19851, 209

0 I1 THF, - 6 3 ° C Cp ( C 0 ) 2 F e C C H 3 + Cp ( C O ) 2 FeCCH2CH2CH=CH2 2 . CH2=CHCH2Br 54% -63 - -20°C Tetrahedron Lett, (1985), 2845 Brinkman, K.; Helquist, P.

II

1 . LiN(TMS)2

*

26,


SECTION 177

0 It

0

II

Me2CHCCHN2

1 . PhH, R h ( O C C F 3 ) 2 RT, l h 2.

CF3COOH, 2h,

CH2C12

0

It

*

Me2CHCCH2 P h

RT

86%

McKervey., M . A . * ; Russell, D.N.: Twohig, M.F. JCS Chem Conm, ---

4

(1985), 491

bPh

AcO

P h B r , cBu3SnOMe,

0

PdC12fP \ Me0

/

100°C

3 ) 2 3 PhCH3 5h

*

54%

)t

Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T.

--Bull Chem Soc *,( 1 9841, 57, 242

0 11

f(CH2)5CH3 FH2 COCH2CH=CH2

I/

Pd(OAc)2,

PPh3

dioxane,

r e f 1 ux

NH40CH0,

35 m i n

* Tsuji, J. ; Nisar, M.;

0

Shimizu, I.

--J Org

1 . CH3MgBr, -70°C, NO 2

2.

*

DDQ,

Chem, (1985),

0

11

CH3(CH2)5CCH3 99%

50,

341 6

THF

10 min O°C,

3h

Bartoli, G. ; BOSCO, M.; Dalpozzo, R. Tetrahedron Lett, (1985),

n02 80%

26, 115

K E T O N E S FROM KET0NE.S

SECTION 177

n-

PhCCH2SiMe3 Fiorenza,

A.

0

BnBr, C s F

It

I1

*

RT, THF, 1 2 h

* M. ; Mordini,

229

PhCCH2CH 2P h

7 0% A.: Papaleo, S.: Pastorelli, S.; Ricci,

-


1 . E B u L i , -5°C 2. E C ~ H , ~ I ,R T 3 . C B u L i , -5°C

CH3CCH3

4. B n B r , R T 5. a q . H C 1

*

CH3(CH2)5CCH2Bn

*

94%

--- a,(1985), 2,407

Yarnashita, M. ; Matsumiya, K.: Tanabe, M.: Bull Chem Soc

nBu3SnH, PhH AIBN Ii I(CH~)~CCH=CH~ reflux, 3h 0

Porter,

* N . A . ; Magnin,

0

II PhCCHPh

1.

Leone-Bay, A.

*

*

Suemitsu, R.

+ oI1

I(CH2)6CCH

Ph2PLi, THF

J Org Chem, (19861,

CH

21CH2)7 H C = C H C? 22%

D.R.; Wright, B.T. J Am Chem Soc, (1986), ----

2. A c O H , M e 1

I

OH

26, 787

108,2787 0

t

2,2378

II

PhCCH 2Ph 76%

SECTION 177


SeMe

I

K-10 c l a y , F e ( N 0 3 ) 3

n C 6 H , 3-C-SeMe 1 Me

pentane, RT, 90 m i n

* Laszlo, P. ; Pennetreau, P.;

*

nC6H,3CCH3 90%

Krief, A.

-

Tetrahednxl Lett, (1986),

C H =C,I0s iMe3

1 . Py, C I O '~C , N 3~. 5 h+ B F ~ 2. aq. H

Ph

w

t

Sakakura, T.; Hara, M.; Tanaka, M.

2,3153

gPh \

73% CI

*

JCS Chem Cum, ---

(1985), 1545

Reviews: tfHmenol ate Aniens" Werstiuk, N.H.

*

Tetrahedmn, (19831,3,205

"1 ,2-Carbonyl Transpositions"

Kane, V.V.

* : Singh, V.;

Martin, A.; Doyle, D.L. Tetrahedron, (1983), 3,345

flAlkylationof Ketones and Aldehydes via Nitrogen Derivativesfl Whitesell, J.K.; Whitesell, M.A.

Synthesis, (1983 , 517

ffReactiveEnolates from Enol Silyl Ethers" Kuwajima, I.; Nakamura, E.

Accts Chem Res,

18, 181 (1985) -

Ketones may also be alkyated or homologated via olefinic ketones (Section 374). Related Methods: Aldehydes from Aldehydes (Section 49)

SECTION 179

SECTION

KETONES FROM OLEFINS

178: Ketones

Nitriles

1 . L D A , T H F , -78°C 2 . 0 2 , - 7 8 " C , 30 m i n

3. S n C 1 2 , a q . H C 1 , 0°C 4 . 1 M NaOH

CN

QPh

Freerksen,,R.W.; Watt, D.s.~

t

Selikson, S.J.; Wroble, R.R.: J Org Chem, (19831,

c

Ph

DMSO,

65%

Kyler, K.S.;

48,

*

Kulp, S.S. ; McGee, M . J .

nPrCH'

OH

1

n Pr CH CH *CH 2CN

*

J Org

2.

/o"" \

93%

Chem, (19831,

80% a q . A c O H lh

J Org

179: Ketones

Set, L.

Chem, (1984),

g , 4097

66%

$9, 1313

Olefins

0

0 2 , PdC12, 8 O o C

CH3(CH2)7CH=CH2

Br

Ph

1 . PhH, Ph3SnH, 15h AIBN, reflux

Clive, D.L.J. ; Beaulieu, P.L.: SECTION

4087

t

02, HOH

K2C03, o v e r n i g h t

Br

-

231

CuC12*2H209 PhH Et3Ncetyl B r , H O H

J a n u s k i e w i c z , K.; A l p e r , H.

~

*

-

II CH~(CH~)~CCH~

-

73%

Tetrahedm Lett, (19831, 24, 5159


n

SECTION 179 n

1 0 atm CO c o ,L (. C O ) 1 0 atm H 2 , 20h n ,

I

1 2OoC, h e x a n e 7 6%

Eilbracht, P.x: Acker, M.; Totzauer, W. Y

*

-Chem Ber,

(19831,

Eilbracht, P. ; Balss, E.: Acker, M.

nC8H, 7 C H = C H 2

116,238

25, 1131


1 . PdCl L" , CuCl , RT 02,DMF:H20, 24h

0

I1 n C 8 H 1 7CCH3

-

2 . 3N HC1

c

Tsuji, J . ; Nagashima, H.: /

ZrCp2

* Nemoto, H.

73%

Org Syn, (19841,

62,

1 . 3 CH C H 2 C H 2 C H = C H 2 3 P h H , 3OoC, 2h 2 . C O Y -78OC, 3 . AcOH

6h

68%

Yasuda, H.; Nagasuna, K.; Akita, M.; Lee, K.; Nakamura, A. Organmetallics, ( 1 984 1, 3, 1 470 1 . NaBH30Ac, T H F , 50°C 2 . NaOMe, CHC13, 5OoC

*

-,,,

3 . H 2 0 2 , NaOH

Narayana, C.; Periasamy, M.

*

-

5 9%


26, 6361

Review: llSyntheticApplications of the Palladium Catalyzed

Oxidation of Olefins to Ketones"

*

Tsuji, J.

9


SECTION 180

233

KETONES FROM M I S C .

See also: Ethers and Epoxides from Olefins (Section 134) and Ketones from Ethers and Epoxides (Section 174). SECTION 180: Ketones from Miscellaneous Compounds

Conjugate reductions and reductive alkylations of enones are listed in Section 74 (Alkyls from Olefins). 0

/CH 3

Ni(R),

PhCH=C

aq.

\

N02

EtOH,

pH 5

It

*

NaH2P02.xH20

PhCH 2 C C H

40-60°C

2h,

88%

*

Monti, D. ; Gramatica, P.; Speranza, G.: Manitto, P. Tetrahedron Lett, (19831,2,417 1 . e-, fH3 nC6H13CH=C -

a q . HC104

\

2.

* : Tanaka, H.;

Katoh, T.

1 . LiBH=Bu3, THF,

Mourad, M.S.: Varma, R.S.:

81 %

-Chem Lett,

(19831, 607

THF

RT

4N H 2 S 0 4 ,

_?C6H1 3 C H 2 C C H 3

>

3% a q . HCHO

Torii, S.

2.

0 II

Pb e l e c t r o d e s CH2C1 2 / d i o x a n e

-10°C

>

* Kabalka, G.W.

Synthesis, (1 985>, 654

81 %


1 . F B u L i , OOC, l h 2 . B n B r , - 7 8 - 20°C, 2 d

N=CHEt

I

HN I CMe3

3. T F A , 2 O o C , 6 h

4. (COOH)2,

aq.

*

SECTION 180

0

II CH3CH2CBn

*

Et20, 14h

67%

Adlington, R.M.; Baldwin, J.E. ; Bottaro, J.C.; Perry, M . w . D . JCS Chem Comn, (19831, 1040 ---

1 . LDA, THF MMe 2 . nC H CH,B,y 6 13

CN I PhCHNM e 2

0 I1 ,llCgH1 3 PhCCH.

HMPT

b

\ 3. a q . H 2 S 0 4 70% CH3 4. A g N 0 3 ( 7' 6 % Hebert , E.*; Maigrot, N.; Welvart, Z. Tetrahedron Lett, ( 1 I

(S)

N-~Bu II Me2N-C-NMe

NO,

COOH

CH,C1 ,, RT * L L Barton, D.H.R. ; Motherwell, W.B.: Zard, S.Z.

-


CH3(CH

) CH N O

1. nBuLi, THF -90 - - 3 o o c

*

0

95%

2, 5227

;-OH CH3(CH2)4CCH2Bn

2.C1HC=NMe2'C13. B n C H 2 M g B r , C u I 97% THF, -3OoC, 2 h * Fujisawa, T. ; Kurita, Y.; Sato, T. -Chem Lett, (19831, 1537

SECTION 180

KETONES FROM MISC.

acetone,

5

LBuOK

235

\

NO2

Iwasaki, G . : Saeki, S.; Hamana, M.

N02

HC02Na,

I

IC$-$5;H

e

CH C H C C H 3

211

Nokami,

8h

0

I1

*

I C ~ H ~5CFH2

T.:

CH 3 C

0

90%

Synthesis, ( 1983), 763

DMF,

0

KI

80"C,

CH3 (CH2

II

5 C ( CH2) 5 C H 3

2 . a q . HC1

Ryu, I . : Ryang, M.;

CH2

\\

20°C Wakabayashi, S.

1. Ni(C0)4, CH3(CH2)5HgBr

MeOH

Chem Lett, (1986), 31

P t electrodes

0

* J. ; Sonoda,

-,

*

59%

96%

*

Rhee, I . ; Omura, H.; Murai, S. ; Sonoaa, N .

Syn Carmun, (19841,

2, 1175

Na2Sn02 15 min

Varma, R.S.; Varma, M . ;

*

* Tetrahedron Lett,

Kabalka, C.W.

6" 86%

(19851,

26, 6014


Ne,

N ,CC1 II0

1 . O RT, , N ~2 4Oh , H MeCN , K ~ C O ~

I

2 . AgN03,

,CHC N

1 . "BuLi,

CHS02Ph

2.

THF,

TMS-OO-TMS,

NO2

78%

Tetrahedron=,

E t

I

nC5H,

\

30 min

Kay, I.T.; Glue, S.E.J.

;"

*

THF

aq.

(1986),

2,113

-78OC -78OC-RT

nC5H, C E t

overnight 3 . a q . NaHCO

Hwu,

* --J.R. J Org Chem,

7 6%

-

(19831, 48, 4432

SECTION 18OA: Protection of Ketones

-

See Section 362 (Ester-Olefin) for the formation of enol ethers and Section 367 (Ether-Olefins) f o r the formation of enol ethers. May of the methods in Section 60A (Protection of Aldehydes) are also applicable to ketones.

A

a

5- , -:

-

1 . 2 HSCH2CH2SH

-

ZnOTf,

OSiPh2tBu2.

reflux,

2h

bqh *

THF/hexane

ZnBr2,

3. BnBr,

Saigo, K. ; Kasahara,

85%

2, 169


1 . LDA,

4 . H 0'

S QOSiPh2LBu

U

* Corey, E.J. : Shimoji, K. 2.

-t

23°C

0

OMe

0-

RT 0°C

-

reflux

*

i.; Ogawa, S.; Nohira, H.

bP 7 9%

(82% ee S )

-

Tetrahedron E ,(19831, 24, 511

SECTION 180A

PROTECTION

1

.

OF

KETONES

237

i B u 2 A l SCH2CH2SA1 i B u 2 PhH, R T , 3 0 m i n

2 . 3M HC1

e

3 . 1 0 % NaOH

Satoh, T.; Uwaya, S.; Yamakawa, K.

’0””’r

LiC104,

e-,

0 0

Q

Chem Lett, (1983), 667

y-y r

CH2C12

Pt electrodes

*

TMSOCH2CH20TMS

* Torii, S. ; Inokuchi, T. 0

*

91 %

Chem Lett, (19831, 1349

0

1 . HOCH2C(Me2)CH20H 0.4M

a q . H2S04

t 2. continuous e x t r a c t i o n Na2C03

Babler, J.H.*; Spina, K.P.

Syn Coamun, (15841,

TMSOCH2CH20TMS, 5h

85%

-78OC

*

2, 39

n

8

Sakurai, H.*; Sassaki, K . ; Hayashi, J.; Hosorni, A. J Org Chem, (1 984), 3, 2808 -

86%


(EtO),Si(CH,),NH,.HCl

-*

Me0

MeOH, R T

3

Me0

97%

Misiti, D.; Palmieri, G. Tetrahedrm, (19841, 110, 1491

Gasparrini, F.: GiOVaMOli, M.: "NMe,

mc p b a

\\d'

Duraisarny, M.:

DMF, Walborsky, H.M.

-63OC quant.

*

--J Org Chem,

(1984),

Gravel, D.*:

Murray, S . : Ladouceur, G.

0

c e t y l NMe3 Mn04-

JCS Chem Comn, ---

*/o H

i-

CH2C12,

RT

2, 3410

90%

(1985), 1828

-8

Vankar, P.; Rathore, R.; Chandrasekaran, S. J Org Chem, ( 1 986), 51, 3063 PhI(OAc),, CH2C12 Moriarty, R.M.*; Prakash, 0. ; Vavilikolanu, P.R. Syn Commun, (19861, 16, 1247

-

98%


CHAPTER 13 PREPARATION OF NITRILES

-

SECTION 181 : Nitriles

I

I

1 atm 5OoC,

Funabiki,

from Acetylenes

H,. HOH d .

i v 85%

10h

* T. ; Yamazaki,

-

I

Y.; Sato, Y.; Yoshida, S. (1983), 1915

JCS Perkin 11, ---

SECTION 182: N i t r i l e s from Acid Derivatives

--

No Additional Examples SECTION

183: Nitriles fran Alcohols -and Thiols No Additional Examples

-

SECTION 184: Nitriles from Aldehydes

-

CHO

1. NH20H-H20, 2.

CS2,

+

PhH,

B u 4 N tH S 0 4 - ,

NaOAc a q . NaOH

RT, 2 0 h

Shinozaki, H.*; Imaizumi, M.: Tajima, M. Chem Lett, (19831, 929

--

l I v 15%

240 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6 OH

SECTION 184

6

0

Me2N C i - Z C l

M e 2 N a , CH2C12

CI

10 m i n

O O C ,

Arrieta, A . ;

* Palmo, C.


0 11 Me3SiO(PO),, Ph-C-H

CI

, DCE

*

r e f l u x , 95 m i n

Aizpurua, J.M.: Palmo, C.

PhCN

92%

Nouv J Chem, (1983), 1,465

*

Nishiyama, K. ; Watanabe, A.

Chem Lett, (1984), 773

S8, NaN02, N H 3

PhCHO

95%

m

1 0 0 ° C , 4h

PhCN 74%

*

Sato, R. ; Itoh, Kao.; Itoh, Kaz.; Nishina, H.; Goto, T.; Saito,

M.

Chem Lett, --

(1984), 1913

SECTION 186

24 1

N I T R I L E S FROM A M I D E S

t

1 . C1 2C=NMe2 C1 DCE,

PhCH 2.

-

RT

-

refiux

e x c e s s PhNH2, RT

-

PhCN

t

DCE

95%

6OoC

3c

Kokel, B. ; Menichi, G.; Hubert-Habart, M. Synthesis, (1985), 201

E t N 0 2 , NaOAc AcOH,

G O M e

t

reflux

4h

*

Karmarkar, S.N.; Kelkar, S.L.; Wadia, M.S. Synthesis, ( 19851, 51 0 SECTION 185: Nitriles from Alkyls, Methylenes, and Aryls

--

No Additional Examples SECTION 186: Nitriles -from Amides 0

II

CH ( CH ) 4 C N H t B u

P0Cl3, reflux,

Perni, R.B.; Gribble, G.W.

PhH 6h

* Org-

*

CH3 ( C H 2 ) 4CN

97%

-Proc Int,

(19831,

15,297

242


:O2Et

CH 2 I NHCHO

1. P0Cl3, CH,Cl9,

iPr2NH

2. Na2C03,

HOH,

Obrecht, R.; Herrmnn, R.; Ugi,

S

2 BnCl,

II

?02et

0°C l h

SECTION 186

CH 1 2 NE C

RT

* I.

+

-

84%


PhH

Bu4NBr

80%

*

Funakoshi, Y.; Takido, T. ; Itabashi, K. Syn Comnun, (19851, 0 --

9, 1299

I1

1. C13CCC1, NEt3 CH2C12, 5°C

0 I1 PhCNH2

* Saednya, A.

2 . HOH 3. NaOH 4. H2S04

t

90%

5 . HOH


0 It

1 . C13CCC1,

0°C

-

PhCN

6°C

O2N

(MeO)3P

-

CN

2. ice/HOH

*

Mai, K. ; Patil, G.

93%

-


3, 2203

NITRILES FROM HALIDES

SECTION 190

243

SECTION 187: Nitriles -fran Amines

No Additional Examples SECTION 188: Nitriles -fran Esters

No Additional Examples SECTION 189: Nitriles -from Ethers, Epoxides,

Thioethers


-

SECTION 190: Nitriles fran Halides

Q I

Suzuki,

1 . NaCH(CN)C02Et, cu I

and Sulfonates ,CN

HMPA

2. a q . N a O H , 90°C

* H. ; Kobayashi,

T.; Yoshida, Y.: Osuka, Chem Lett, (19831, 193 --

HOH, H2, 55OC

* A.

-

24h

*

6 9%

64%

Funabiki, T. ; Nakamura, H.; Yoshida, S. -J Organomet

e, (19831,

3,95


244

nBu3SnCH2CN 1 2 O 0 C Y 3h

xyl ene

PdCl2[P-oTol3I2 Kosugi, M.;

I s h i g u r o , M.:

Sano, H.: Migita, T.

* : Farooq,

*A

CH2C12, r e f l u x 23h 0 . ; Surya Prakash,

78%

G.K.

Synthesis, ( 1 9851, 1 140 \CN

0

I

11

1 . NaCH(CN)P(OMe)2 17OOC - 2OOOC 2. a q . HC1

Suzuki,

*

(19841, 151 1

Me3SiCN, A1Br3

Olah, G.A.

Q

*

78%

Negishi, Y.;

Chem Lett, --

SECTION 191

* H. ; Watanabe,

K.:

Y i , Q.

* -Chem Lett,

59%

(1985), 1779

SECTION 191: Nitriles from Hydrides

1 . DMF, P0Cl3 OMe

2. NH40H-HC1

Liebscher, J.; Bechatein, U .

*

Zeit Chemie, (1983),

OMe

43%

23, 214

SECTION 193

245

N I T R I L E S FROM N I T R I L E S

SECTION 192: Nitriles f'ran Ketones

-

-

1 . SnC14,

EtS SEt V

U

2.

Me3SiC

Ni(R)

30% Reetz, M.T. * ; Muller-Starke, H. Tetrahedron Lett, (19841, 3, 3301

-

SECTION 193: Nitriles fran Nitriles

Conjugate reductions and Michael alkylations of olefinic n i t r i l e s ar e found i n Section 74D ( A l k y l s from Olefins). A1 203/KOH , E t B r Ph CH 2 C N

Sukata, K.

PhH,

*

40"C,

CN

I

*

4h

PhCHCH 2 C H 91 I

WiLl Chem Soc Jpn, (1983), 56, 3306

---K

+

-

Me2C-N02,

DMSO

*

1 .75h

Kornblum,

* N . ; Singh, 1.

74%

J Org Chem,

PhCH2C1, N i * ,

BrCH2CN

Ni

*

Boyd, S.D. (1984),

H.K.;

85"C, 2 . a q . HC1

30h

3, 358

glyme

*

= activated nickel

Inaba, S.; Rieke, R.D.

*


P h CH 2 C H 2 C N

57%


SECTION 195

1 . IBu3SnLi, -78OC

CN

HMPA,

I

Ph- C-SEt

2 . BnBr, THF,

I

CH 3

THF,

3. 1 N N a O H

*

Takeda, T. ; Ando, K . ;

30 m i n

-78°C

CN

-

I

Ph-C-CH2Ph

RT

I

CH 3

87%

Mamada, A.; Fujiwara, T. Chem Lett, (1985), 1149

--

SECTION 194: Nitriles fnw Olefins No A d d i t i o n a l Examples

SECTION 195: Nitriles from Miscellaneous Compounds

gJ-

Me3S i I , C H 2 C 1

NO*

Olah, G.A.

25"C,

* ; Narang, /

16h

t 98%

S.C.; F i e l d , L.D.; Fung, A.P. J Org Chem, (1983), 2766 ---

s,

1 . NaCN, 2.

25"C,

Pb(OAc)4 -2OoC,

-6

5 min

12h

88%

Masuda,

Y.;

Hoshi, M.;

*

Yamada, T.: Arase, A . JCS Chem Comn, (19841, 398

---

SECTION 195

N I T R I L E S FROM M I S C .

FVP 540°C,

N=C +

-

Meier, M.; Riichardt, C.

*

247

Torr) 25 m i n

97%

-


CN

25, 3441

T1 ( t f a ) ,

*

Taylor, E.C. ; Katz, A.H.: McKillop, A. Tetrahedron E ,(19841, NS i M e 3

II

P h C 0 s iMe

n~ u 4~ + F -

15"C,

20h

72%

3, 5473

m

PhCN quant.

*

Rigo, B. ; Lespagnol, C.: Pauly, M. Tetrahedron E ,(19861,

Murahashi, S.-I.

* : Naota, T.; Nakajima, N. J Org Chem, (19861, 51, ---

3,347

94%

898


CHAPTER 14 PREPARATION OF OLEFINS

-

SECTION 196: Olefins from Acetylenes

-

1 . iBuMgBr

CH3(CH2)4CECSiMe3

*

CH 3 ( C H 2 ) 4

Cp2TiC1 2. CH2=CHCH2 CuI, CH21

e

\

/SiMe3

c=c,

FH

H’ 2 86% H2C=CHkHi

Sato, F. ; Watanabe, H.; Tanaka, Y.; Yamaji, T.; Sato, M. Tetrahedron Lett, (1983), 24, 1041

NaBH4-PdC1

P h - C=C

-Ph

Suzuki,

* N. : Tsukanaka,

PEG, CH2C12, PEG = p o l y e t h y l e n e g l y c o l

FeC12,

91 %

---

c,( C H S-S

*

P h CH = C H P h

T.: Nomoto, T.; Ayaguchi, Y.; Izawa, Y. JCS Chem Carm, (19831, 515

NaBH4, E t O H , Ph-Cs-Ph

*

30 m i n

Kijima, M.; Nambu, Y. ; Endo, T.

35OC, 8h

> )4hNH 0

*

7 5%

Chem L e t t , (19851, 1851

OLEFINS FROM ACETYLENES

SECTION 196

HCnC

Ph PhZnCl , T H F qH Et20 C02Me

Elsevier, C . J . :

*

3% Pd(PPh3)q

,\

= c\

Et20

1

CH 3 C H = C C H = C H

3. L i , - 6 0 ° C - 2 0 ° C 87% * Barluenga, J. ; Yus, M . ; Concell6n, J.M.; Bernad, P. J Org Chm, (1983), 3,609 --+PPh3 I

+ C ;OOH

Et02CN.NC02Et

* (I:E =

i P r CH = C H P h 98:2)

73%

*

Mulzer, J . ; Lammer, 0.

Angew Chem Int Ed Engl, -----

(19831,

22,

628


1 . CH2N2, 2 . HC1,

i PrCH2CC1

:

Barluenga, J.

Et20,

-20°C

Et20, overnight

E t I

0°C - RT iPrCH2C=CH2 3 . E t M g B r / M g B r 2 , THF 4 . L i , RT, o v e r n i g h t 75% Yus, M.; Concellon, J . M . : Bernad, P. J Org Chem, (19831, 48, 3116

-

P b ( OAc )4, C U ( O A C ) 2 * H 2 0

,,#+

OcooH DMF-AcOH,

SiMe,

Nishiyama, H.

SECTION 198

*

RT,

t

3h

72%

; Matsumoto, M . ; Arai, H.: Sakaguchi, H . ; Itoh, K . Tetrahedron Lett, (19861,

3, 1599

SECTION 198: Olefins from Alcohols and Thiols

-

-

--

CH3CN/Na I

0

Me3SiC1

Sarma, J . C . ;

@

HO

D'Onofrio, F.:

60%

10 min

OMe

Sarma, D.N.;

, RT

0 t

Sharm, R.P.

Barua, N.C.;

*

0

JCS Chem Conm, (1984) , 81 3 ---

l:sOH/SiO:h ref1 ux,

S c e t t r i , A.

*

~

@

17

97%

Synthesis, (19851, 1159

SECTION 199

O L E F I N S FROM ALDEHYDES

Fadel, A,; Salaun,

* J.

253

92%

Tetrahedron, (19851, 41, 1267 Tetrahedron, (19851, 3, 413

0

II

1 . C1P(OiPr)2, 2 . NaFp

Py

*

3 . HBF4

OH

4. NaI

Araki, S.;

Hatano, M.; Butsugan, J Org Chem, (19861,

---

1 . CH(OMe)3,

THF,

OHt i

0

2. sealed tube,

Ando, M.

24%

* Y.

* ; Ohhara,

140°C,

3

e

Ac20,

*

H.; Takase, K.

P 2h 3 PK 2 CC H0 32 P, r MeOH

1 .5h

90%

1.5h

Chem Lett, (19861, 879

t

25OC,

2126

12h

SECTION 199: Olefins from Aldehydes

b C H 0

51,

&

CH =CH P r

w

( & : I=

78%

82:18)

Le Bigot, Y.: Delmas, M.; Gaset, A. Tetrahedron Lett, (19831,

2,193

254 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6 +-

SECTION 199

0 It

Ph3PCHCCH2CH2C02Me, D M F , 2 5 O o C , 22h Ronald, R.C.; Wheeler, C.J.

*

0 / '

2 C1Mo3c.i , T H F , -70°C 2

J Org Chem, ---

(19831, 48, 138

-

RT ____t Kauffmann, T.*: Fiegenbaum, P.; Wieschollek, R.

C H ~ ( C H ~5~~~ )

2. HOH

84%

(19841, 23, 531

Angew Chem Int Ed Engl, ----

1 . C13Mo=CH2, THF Et20, -70 - 20°C

70%

____t

t

CH3(CH2)5CH=CH2 6 5%

Kauffmann, T.; Enner, B.; Sandler, J.; Wieschollek, R.

----Angew Chem Int Ed -1,

(19831, 22, 244

1 . ( iPr0)3TiCH2CH=CHPPh2 - 7 8 O C - 0°C 2. M e I , 0°C

-

RT

(E:Z iFUkai, J.; Ikeda, Y.; Ikeda, N.; Yamamoto, H.

=


-

2 PhCHO

WC16' e - ,

t

4h

Petit, M.; Mortreux,

PhCHO

THF

A.;

Petit, F.

*

Clift, S.M.: Schwartz, J.

=

2, 4029 P h C H = C H Ph 88:9)

97%

* --JCS Chem Comn, (1984),

Cp2Zr(PPh3)=CHCH2tBu PhCH3, 3h

(r:I

4:96)

-t

341

PhCH =CH CH 2 t B u 7 6% (L:L = 1 :2)

J Am Chem Soc, ----

(1984), 106, 8300

SECTION 199

O L E F I N S FROM A L D E H Y D E S

CH212,

C H 3 ( CH ) 5CH 0

Zn, THF

20 m i n

RT,

*

255

C H ~ ( C H ~ ) ~ C H = C H ~

)%9)

71 %

Yamashita, J.*; Inoue, Y.;

Kondo, T . ; Hasimoto, H. Bull Chem Soc Jpn, (19841, ----

+

CH2=CHPPh3 Br-

1 . n-Bu2CuLi, THF HMPA, -5O"C, 9 h 2 . 5C5Hl1CHO

-

-20°C 3 . aq. NH4C1 -50

J u s t , C.:

tB

(Z:E - -

u

26,

1799

P hCH =CHtB u

(I:E =

* R.R,

58%

= 1:4)

*

25°C

2335

n B u C H 2 C H = C H n-C 5 H 1


O'Conno?, B.

PhCHO

t

57,

95%

1:4)

Freudenberger, J.H.; Shrock, Organometallics, (1986), 5, 398

@W I PhCHO

PhH,

25:C,

(OCH t B u ) 25 min

Aguero, A.; Kress, J.; Osborn, J . A .

t

D

C

HPh

88%

--JCS Chem Carm, (19861,

Related Methods: Olef i n s from Ketones (Section 207)

531

256 COMPENDIUM CF ORGANIC SYNTHETIC METHODS VOL 6

SECTION 201

-

SECTION 200: Olefins -from Alkyls, Methylenes, and Aryls

This section contains dehydrogenations to form olefins and unsaturated ketones, esters, and amides. It also includes the conversion of aromatic rings to olefins. Reduction of aryls to dienes is found in Section 377 (Olefin-Olefin). Hydrogenation of aryls t o alkanes and dehydrogenations to form aryls are included in Section 74 (Alkyls, Methylenes, and Aryls from Olef ins). 7.

CH2=CHLBu

2.

(Me0)3P

95%

Baudry, D.* ; Ephritikhine, M.*: Baudry, D.*: EphritiWine*

I.

Felkin, H.; Zakrzewski, J. Tetr edron Lett, (19841, 25, 1283

e kin, H.; Holmes-Smith, R.

JCS C h a CODIII, (1983), 788

---

C H ~ N H ~D,E A ,

Ca

-25OC 2 . Et20, a q . N H 4 C 1

>

A+ 7 6%

* Benkeser, R.A. : Belmonte, F.G.; Kang, J. J Org Chem, (19831, 48, 2796 ---

'I!,

"+,

2 0%

SECTION 201 : Olefins -from Amides

No Additional Examples Related Methods: Alkyls and Aryls from Alkyls and Aryls (Section 65) Alkyls and Aryls from Olefins (Section 74)

SECTION 203

O L E F I N S FROM ESTERS

257

-

SECTION 202: Olefins -from Amines

No Additional Examples SECTION 203: Olefins -from Esters 1. nBuLi

II0 Ph2PCH2CH2iPr

2.

PhC02Et

3.

NaBH4,

EtOH

*

PhCH=CHCH2i P r

4 . N a H . DMF

49%

*

Buss, A.D.; Mason, R . ; Warren, S. Tetrahedron Lett, (1983),

2, 5293

1 . LDA "CgH17

CO2E t

2.

Ph2MeSiC1

3.

LiA1H4

___)

nC8H1 7CH=CH2

4 . B F 3 - O E t 2 , CH2C12

De Maldonado, V.C.; Larson, G.L.

32OoC,

*

Syn Caunun,

85%

(1983),

13,1163

sealed tube

1 .5h JPh OMe

OMe

Chwchaang, W.: Chantarasiri, N.; Chaona, S.; Thebtaranonth, C."; Thebtaranonth, Y. Tetrahedron, (19841, 40, 1727

55%


1 . 2 MeMgI,

THF

reflux,

24h

/C02Et

2.

3 MeLi,

\

3.

9 ~ B ~ o - K + R, T

nC8H, ,CH -

S i Ph2Me

Hernindez, D.;

*

Larson, G.L.

reflux

SECTION 204

nC8H1 7CH=CMe2 54%

l h

J Org Chem, (19841,

s, 4285

1 . PhMe2Si)2CuLi 2 . LiA1H4

3. G N 0 2 SeCN,

CH3CH=CHC02Et

Bu3P

fH3 PhMe2S i C H CH=CH 50%

4. H202

*

Fleming, I . ; Waterson,

D.

1. 0'

P hCO 2 E t

*

2 . NaBH4,

--JCS Perkin \I CeC13,

I, (19841, 1809

, THF MeOH

-78°C 3.

>

PhCH =CH C H

(g

base

E l l i o t t , J . ; Warren,

* S.

96%


3, 645

SIXTION 204: Olefins from Ethers, Epoxides, p c J Thioethers S

I\

-?'12 H 2 5 C H C H 2

Schauder, J . R . :

P214,

DMF

8OoC,

12h

*

nC, 2 H 2 5 C H = C H 2

97%

*

Denis, J.N.; Krief, A. Tetrahedron Lett, (19831, 2, 1657

SECTION 204

45 rnin

reflux, Martin, M.G.:

Ganern, B.

*

80%

Tetrahedron Lett, (19841,25, 251

nBu3MnLi

&Ph \\\'

,+"

-

-30°C

Ph

* : Bisling,

Kauffrnann, T.

CH3 ( C H 2 ) 5CH-CH2

Barton, D.H.R.

0

nC5H1

/ \

66%

EtOH

ref1 u x

t

CH3( CH,),CH=CH2 92%

; Fekih, A . ; Lusinchi,

X.


PhCNH2,

CH-CHCH3

r

Ph

Tetrahedron Lett, (1984),3,293

M.

2. PyH*OTs 3c

.Ph

1

*

RT

1. NaHTe,

0

/ \

-

259

O L E F I N S FROM E T H E R S

0°C

CF3COOH,

CH2C1

P

26,

nC5H1

Miyake, J.; Murai, S.;

CH=CHCH3

74%

10 rnin

Ogawa, A.:

6197

3c

Sonoda, N . Tetrahedron Lett, (1985),

26,

669


260

-

Sulfonates

SECTION 205: Olefins from Halides

-

SECTION 205

I

,

CH 2=CH

N iI

( PPh3 )

> 8 0%

R o l l i n , Y.: Meyer, G . ; Troupel, M.; Fauvarque, J . - F . ; J.

--JCS Chem Cam,

MeOH,

Br

@= Janout,

1% dvb,

(1983), 793

50°C

*

3.5h

@CH2S-Naf,

Perichon,

9 5% ( 9 9 ) c o - d i v i n y l benzene]

poly[styrene

v.;

v

Cefelln, P.

1.

Tetrahedron E ,(19831,

(PhTe)2,

NaBH4,

2,391 3

EtOH

r e f 1ux 2.

Br2,

CC14,

3 . a q . NaOH,

0°C 25°C

3h

Uemura, S. c1

I

* : Fukuzawa,

S.

---J Am Chem Soc,

1 . CH2=CHBr,

,

NiC12, Et20

PPh Me2N-CH C H \ CH2SMe

PhCHCH3

62%

, RT

(19831, t

105,2748 PhCHCH=CH2

90% (23% ee, S ) 1 0 % HC1, j 0 C G r i f f i n , J.H.; Kellogg, R.M. J Org Chem, (1985), 50, 3261 2.

SECTION 205

OLEFINS FROM H A L I D E S

261

1 . Mg, E t 2 0 p

cat.

h

CI

2.

y

ZnC12,

3 . CH2=CHBr,

THF/Et20

cat.,

Ph

*

THF/Et20 0°C

9 5% (85% ee, S )

=

*

Hayashi, T.; Hagihara, T.; Katsuro, Y.; Kumada, M. will Chem Soc *,(1983), 56, 363 Hayashi, T. Konishi, M.; Okamoto, Y.; Kabeta, K . ; Kumada, M. J Chem, (1986), 2,3772

---

*:

I

Br

1 . C8K,

I

PhH, R T ,

8h

2 . EtOH

PhCHCH2Br

t

3 . HOH C8K = g r a p h i t e powder/200°C/K Rabinovitz, M.

* ; Tamarkin,

Br I PhCHCHPh

I

B r

D.

PhCH =CH 8 0%

Syn Cornnun, (19841,

a q . Na2S.9H20,

111, 377

PhCH3 PhCH=CHPh

-t

Bu3P+C1 6 H 3 3 B r 25OC, 9 5 r n i n

quant.

Landini, D.*; Milesi, L.; Quadri, M.L.: Rolla, F. J Org Chem, (19841, 49, 152

9

Hrubiec, R.T.;

-

1. nBu2CuLi, -2OOC 2 . HOH

Smith,

* M.B.

-

Et20

\/ e

~-Bu

(E:I =

-

80%

2:l)

J Org Chem, (1984) , 3, 385


SECTION 205

n B u 4 S n , Pd(PPh3)4 2 L i C 1 , T H F , 70°C

t -Bu

S c o t t , W.J.: C r i s p , G.T.;

Br

1B r

Davies, S.G.

*

1 5 min

* ; Thomas,

80%

S t i l l e , J.K. J Am Chem Soc, (1984), ----

Cp2TiC1 2 y T H F

I

nPrCHCHCH3

-

t-Bu

41h

S.E.

106,4630

t

9 5%

Synthesis, (1984), 1027

1 . L B u L i , T H F , -78°C NNHTRIS II Li2CuC1 CH~C(CH~)~C~ 2. O"C, 10 m i n Charnberlin, A.R.

*

Bloom, S.H. Tetrahedron

Br

nPrCH=CHCH3

66%

E ,(1984) , 25, 4901

1 . HOCH2SO2-Nat-2H20 Te, EtOH, NaOH, 70°C 2 . 2M H C 1

Suzuki, H.

* ; Inouye,

M.

Chem Lett, (19851, 225

77%

SECTION 206

263

OLEFINS FROM HALIDES

Q I

6e3

CH2=CHSiMe3, P d ( O A c ) *

PPh3 5 0 ° C , 5h

AgN03, C H 3 C N ,

NEt3,

*

67%

Karabelas, K.: Hallberg, A. Tetrahedron Lett, (1985), 26, 3131

-

1 . i B u 3 A l , 30 m i n *--/

Br

Ni(MeSa1 )2

e

2 . d i l H2S04 MeSal = !-methyl

-+-. i-BU

pentane, RT

91 %

salyc i l a l dimine

Caporusso, A.M.*; Da Settimo, F.: Lardicci, L. Tetrahedron Lett, (1985), 26, 5101 (Me3Sil3MnMgMe

BrC h = C H P h

(I)

Fugami, K.;

-

Et20/THF, -78"C,

3h

>

PhCH=CHSiMe3

(2)

Oshima, K.*,' Utimoto, K.: Nozaki, H. Tetrahedron Lett, (1986),

70%

2,2161

-

SECTION 206: Olefins from Hydrides

No Additional Examples For conversions of methylenes to olefins (RCH,R' Section 200.

+

RR'C=CH,, see


SECTION 207

SECTION 207: Olefins fran Ketones

0

+-

II

( M e S ) 2BCH2

PhCPh

t

Ph2C=CH2

75% Pelter, A . ; Singaram, B . ; Wilson, J.W. Tetrahedron E ,(19831, 24, 635 0

C p 2 T i C H 2 .ZnI

II

PhCPh

Eisch,

PhCH3,

* J.J. ; Piotrowski,

t

-1OOC

Ph2C=CH2

78% A.

-


Cp2Ti 0°C

Et20,

-

t

RT

Bh Clawson, L.;

Buchwald, S.L.; Crubbs, R.H.

Bernard, M.; Ford,

*

-


* W.J.

0

84%

25, 5733

99%

--J Org Chem,

(19831, 48, 326

SECTION 207

265

O L E F I N S FROM KETONES

1 . N H 2 N H S 0 2 P h , MeCN-HC1 2.

2.2 E B u L i ,

3.

0°C

-8°C

t

4 . EBuBr, 2 0 ° C overnight Chamberlin, A.R.

Baba, T.:

*; Liotta,

50%

E.L.; Bond, F.T.

Org Syn, (19831,

* --Bull Chem Soc s,(19831, 56,

82%

Avasthi, K.; Suzuki, A.

2. d e c a l i n ,

2h Mohmadi, F.: C o l l m , D.B.

*

92%

THF,

-7aoc

t-Bu

82%

* S. ; Delorme,

25, 271


Me

KDA,

1571

160°C

0

Hanessian,

61,141

ii

t

t-Bu (95

D . ; Beaudoin, S.;

---J Am Chem

Leblanc, Y .

-

:

Soc, (19841, 106, 5754

t-BU

5)


SECTION 207

84%

Murayama, E . ; Kikuchi, T.; Sasaki, K . ; Sootme, N . ; Sato, T . Chem Lett, (19841, 1897

--

1 . LDA

0

II

CH3(CH2)9CCH3

Takai, K . ; Sato, M.:

t

E t

2.

C1-b(OPh)2 0

3.

2 Et3A1,

25°C

Pd(PPh )

,

*

I

C H ( C~ H 2 ) g~~ = C H ~

71%

3h

Oshima, K.'; i o z a k i , H. B u l l Chem Soc Jpn, (19841, 57, 108 ----

tBuO-K',

Ph3PMe,

PhH

100°C,

2h 91 %

add k e t o n e t o m i x t u r e t

F i t j e r , L. ; Quabeck, U.

-Syn Comrmn,

(1985),

3,855

0

1. LiN(TMS)2 2. B E t 3

3 . CH2=CHPPh3+Br4 . KOH

Posner, G.H.

t

; Lu, S.-B.

J Am Chem ----

*

ph$?:"2

-

Soc, (19851, 107, 1424

69%

SECTION 209

1 . C1CH21, -78

MeLi

- -60°C

-

2. Li, -60

Barluenga,

267

O L E F I N S FROM O L E F I N S

t

20°C

* J. ; Fernandez-Simon, J.L.: Concellon, J.M.; JCS Chem Comn, (1986), 1665 ---

8 0%

Yus, M.

Review: "Titanium Induced Dicarbonyl-Coupling Reactions1'

McMurry, J.E.

*

Accts Chem Res, (19831, 16,405

I -

Related Methods: Olefins from Aldehydes (Section 199) 208: Olefins from Nitriles SECTION 1 . LDA,

CN

THF,

-78°C

2 . nBu3SnCH21,

I

"C12H25CHCH3

3.

MeLi, THF,

*

-78

LiBr/Et20

Me

- 0°C t

I

"C1 2 H 2 5 C = C H 2

-20°C

83%

4 . a q . NaOH

Pearlman, B.A. ; Putt, S.R.; Fleming, J . A . --J Org Chem, (1985), 2,3625 SECTION 209: Olefins from Olefins 1. nBu3SnLi PhS02CH=CHnC8H1

2.

CHC13, S i 0 2 t 6OoC,

Ochial, M.; Ukita, T.: Fujita,

* E.

nC8H1 7 C H = C H

17h

2

78%

JCS Chem Ccnun, (19831, 619 1 457

C h e m m t T 9 8 3 1, --


FP+

1 . CH2C12, HBF4.0Et2,

cH IcH I

2 . NaI, a c e t o n e

I

3 . HC1,

(CH2)4

4 . "BuNI,

CH1Cy2 FP

Lennon, P . ; Rosenblum, M.

4

0°C

CH2C12, RT, 4 h C H 2 C 1 2 , RT

52%

* 2 Am

2h

v

(Me3Si)3A1.0Et2

; Yoshida,

J . ; Lautens, M.

J Am Chem ----

Soc,

105, 1233

72%

reflux x

YiMe

Chem Soc, (1983),

M o ( C O ) ~ , PhCH3,

Trost, B.M.

SECTION 209

(E:l (1983),

/

= 2:l)

105,4494

C p 2 T i C 1 2 , THF iPrMgBr, 20°C

7 6%

lh Lehmkuhl, H.

* ; Tsien,

ll

Y.-L.

*

3(

16%

Chem Ber, (1983), 116, 2437

1 . Cp2Ti

t 2 . PhCPh, PhH, RT, 1 2 h I1

0 Buchwald, S.L.;

Grubbs, R.H.

* ---J Am Chem

80%

Soc,

(1983),

105,5490

SECTION 209

N0

I

-

CH3

Ono,

Et,OL

-30°C

* N. ; Hamarnoto,

PhCH2CH=CHCH3

6OoC,

* ; Viout, P.

c

CH 3

I CB u CH CH = C C H

cl

,C.02Et

7 6%

RT

15h I.; Kaji, A .

10 KOH,

D'Incan, E.

-

269

OLEFINS

nBu 2CuL i

CH =CH - C CH 2 C H C O 2 E t* - .

I

FROM

OLEFINS

( -E :_Z = 8 8 : 1 2 )

--JCS Chem Comn, (19841,

DME 30 min

*

274

PhCH =CHCH2CH3

95%

Tetrahedron, (1984),

$0,4321

- s i : e 2 8

PhMe2SiMgMe

ZPh

cu I

1-

O"C,

12 min

(95

*

Morizawa, Y.; Oda, H.; Oshima, K. ; Nozaki, H.

-

Tetrahedron Lett ,. (19841,

1 . O=S=NSO P h ,

2

0 - 20"C,

2 . EtMgCl,

5) 74%

3,1163

Et20 10h

CuBr/Me2S

*

3. aq. H+

*

Deleris, G. I Dunogues, J.; Gadras, A .

Tetrahedron Lett, ( 1984),

80%

25, 21 35


PhHgCl , CuCl (PhS02)2C(CH2CH

L

L

* Trost, B.M. ; Burgess, K.

10% P

SECTION 210

PhS02

P Y B n

L

THF R T

50%

JCS Chem Camn, (1985), 1084

- 6

S0,Ph

DMF

PhSO2Na*2 H20,

6"O'

5% Pd(PPh3)4,

20°C

70%

1 Oh

t

Ono, N. ; Hamamoto, I.; Kawai, T.; Kaji, A.; Tamura, R.*: Kakihana. M. B u l l Chem Soc *, (1986), 405 --* Tamura, R.*; Hayashi, K.; Kakihana, M.; Tsuji, M.; Oda, D.; Scholz. D . Tetrahedron Lett, (1985), 26, 851

z,

SiMe, SO,Ar

1. nBuLi, 2.

THF,

-78

- 0°C

a q . NH4C1

*

Padwa, A. ; Wannamaker, M.W. Tetrahedron Lett, ( 1 9861,

90%

3,581 7

-

SECTION 210: Olefinz from Miscellaneous Compounds NaTeH,

RT,

*

EtOH

lh

Osuka, A. ; Shimizu, H.; Suzuki, H.

*

86%

Chem Lett, (1983), 1373

SECTION 210

OLEFINS FROM M I S C .

271

1 . NaH, E B u L i

0

II

PhCCH2S02Me

2 . cC8H171

Scholz, D.

7 5%

reflux

EtOH,

Liebigs Ann Chem, (1 9831, 98 1 . EBuLi,

0

II

PhCH2SPh

II

0

Engman,

L

4 . NaOEt,

*

nC8H1 7CH=CH2

+

N a O H , Br,

3.

THF,

0°C

2.

24% T e ,

RT,

3.

50% a q .

AcOH

* -J Org C h m , L.

NNHTs

( 1 9841,

3h

90%

(I:E =

Ph

diglyme t

PhC(CH2)40H

2.

Harada, T.; Akiba, E.: 651

8OoC,

Oku, A.

6h

*

-

Varbene Complexes i n Organic SynthesisfT

---

Angew Chem Int Ed -,

(1984),

"The Peterson Reactionf' Ager, D.J.

*


"Recent Developments i n Alkene Chemistry" Pasto, D . J .

*

74%


Reviews : D B t z , K.H.

2:8)

2, 3559

1 . 2 . 2 KH,

II

PhCH =CH Ph

t


2, 2805

23, 587

26,


CHAPTER 15 PREPARATION OF OXIDES

This Chapter contains reactions which prepare the oxides of nitrogen, sulfur, and selenium. Included are g-oxides, nitroso, nitro compounds, nitrile oxides, sulfoxides, selenoxides, and sulfones. Oximes are found in Sections 60A (Protection of Aldehydes) and 180A (Protection of Ketones). Preparation of sulfonic acid derivatives are found in Chapter Two and the preparation of sulfonates in Chapter Ten. Oxides from Acetylenes - --

SETION 211


---

SECTION 212: Oxides from Acid Derivatives


--

SECTION 213: -Oxides from Alcohols and Thiols

PhCH2CH2S-Na

2 . KMn04,

a q . AcOH

3 . N a B H 4 , MeOH 4 . BnBr

* Ueno, Y. ; Kojima, A . ;

Okawara, M.

*

BnS02Bn 84%

Chem Lett, --

SECTION 214: Oxides from Aldehydes

--


(19841, 2125

SECTION 215

O X I D E S FROM A L K Y L S

273

SECTION 215: -Oxides from Alkyls, Methylenes, and Aryls CH3S02F,

-

50°C

Hyatt, J . A .

A 1 C1

RT,

l h

*

91 %

* ; White, A.W.


PhS03H,

PPA

*

'2'5

Sipe Jr.,

so2 Me

* H.J. ; Clary, D.W.:

White, S.B. Synthesis, (1984), 283

+SO~H 20"C,

56%

. H ~ O

24h

CH3S03H-P205 95%

*

Ueda, M. ; Uchiyama, K.; Kano, T. Synthesis, ( 1984) , 323 FeN03-K-10 c l a y THF,

20h

*

3 9%

41 %

NO,

Cornelis, A . ; Laszlo, P. ; Pennetreau, P. Bull Chem Soc Belg, (1984), 93, 961 ---

274 C0MPEM)ILJM OF ORGANIC SYNTHETIC METHODS VOL 6

SECTION 217

Si02, CAN pet ether,

* Chawla, H.M. : Mittal, R.S.

PhH

6 NO 2

65%

Synthesis, (19851, 70 F

HN03-S i 0 2

&NO:

CH2C1

40%

Tapia, R.; Torres, G . : Valderrama, J.A. Syn Ccxunun, (19861, --

42%

16,681

NO2

SECTION 21 6: --Oxides from Amides

No Additional Examples SECTION 217: ---Oxides from Amines

- ,oo,

(HO)*B,

00’

-

B ( O H ) 2 2Nat.6H20

5 0 % a a . MeOH

*

McKillop, A . ; Tarbin, J.A

H

Mitsui, H.; Zenki, S.:

t


H2°2 Na2W04

*

* Shiota, T.: Murahashi, S. JCS Chem Comn, ---

(19841, 874

92%

9,1505

oj, +Y -

0

68%

SECTION 219

275

O X I D E S FROM E T H E R S

SECTION 218: Oxides from Esters


-

SECTION 219: --Oxides from Ethers, Epoxides,

,oo, PhSCH3

( H O ) 2B,00,B

(OH)

50% a q .

* McKillop, A. ; Tarbin, J.A

PhSCH3 + 74%(1 eq)

-


1

CH3N02,

+

2,1505

COOH

0

,

4h

Helv Chim Acta, ---

Bu4N

PhSCH3 94%(excess)

0

*

It

P h C=CS M e

R u C ~ ~ ( P P ~ ~ ) ~

Miiller, P . : Codoy, J.

B n S C H 2 C H 2CH * B r

0

I1

II

w

4 P h C=CSM e

0

*6H20

MeOH

and Thioethers

aq. HN03

AuC104-

(19831,

t

66,

1790

0

II

B nSCH 2CH 2CH *B r

4h

GasDarrini, F.: Giovannoli, M.; Misiti, D.; Natile, C.; Painieri, C. Tetrahedron, (19831, 2,3181

89%


SECTION 219

OH I

0

CH 3CHOOOH -4O"C,

I1 Pr- S - Pr

t

Pr-S-Pr 30 min

no y i e l d Shereshovets, V.V.; Komissarov, V.D.; Shafikov, N.Ya.; Bachanova, L.A.; Kolosnitsin, V.S.; Nikitin, Yu.E.: Tolstikov, G.A. -J Org Chem USSR, (19831, 2, 207

Ph-S-iPr

2 . HOH

Palmieri, G.

\I

P h - S - i Pr

t

* Gasparrini, F. ; Giovannoli, M.;

93%

Maresca, L.; Natile, G . ;

~ C o m n u n ,(19841, 14, 1 1 1 1

tBuOOH,

PhCH2-S-CH3

0

1 . CH3N02, a q . HN03 a q . H2S04, R T , l h

-

( + ) - d i e t hyl t a r t r a

CH2C12,

, .o

Ti(OiPr)4

-77"C,

tk

P h C H -'S

*

-CH

7 0%

24h

DiFuria, F.; Modena, G.; Seraglia, R.

;

(46% ee) Synthesis, (1984), 325

Ti(OiPr)4, LBuOOH Ph-S-CH3

( R , R ) - d i e t h y l t a r t r a t e>

H O H , -20° C

P'h:/

CH 80%

( 8 9 % eed R ) Pitchen, P. ; Duzach, E. ; Deshmukh, M.N. : Kagan, H.B. J Am Chem Soc, (19841, 106, 8188 *---Tetrahedron Lett, (lm), 25, 1049 Pitchen, P.; Kagan, H.B.

SECTION 220

p" Me3SiOC=CH2

O X I D E S FROM ETHERS

1 . PhN=O,

CHC13,

1 N H C 1 , THF, 2 0 ° C

3.

Ag20,

Sasaki, T.; Mori, K. ; Ohno, M.

P-

20°C

2.

PhH,

*

(+)-diethy1

0

P hCCH=N - P h

80%

Synthesis, ( 1 9851, 279 0

*.

% ",,

*

*

Nouv J Chem, (1985), --0

80 % S)

967

SECTION 220: --Oxides from Alkyl Halides and Sulfonates


R)

2, 1

( 4 0 % ee,

Imarnoto,

Q

60%

tartrate

* T. : Koto, H. -Chem Lett, (19861,

/

PhH'S

t

( 9 5 % ee,

Dunach, E. ; Kagan, H.B.

0

t

I1

t

20°C

T i ( O i P r ) 4 , a q . LBuOOH C H 2 C l 2 , - 2 O " C , 1Gh

S-Ph

277


SECTION 224

SECTION 221 : -Oxides from Hydrides 1 . HgC12,

PhS02Na, HOH RT

2.

50% aq.

NaOH/dioxane

82%

RT Sas,

W.

JCS Chem Comn, (1984), ---

+

6

862

-

N H 4 N O 3 , CH2C12

( C F 3 i ) 2 0 , HBF4 0 35°C

Bloom, A.J.: Mellor, J.M.

*

7 0%

-


SECTION 222: -Oxides from Ketones

No Additional Examples SECTION 223: -Oxides from Nitriles

No Additional Examples SECTION --224: Oxides from Olefins


3, 873

SECTION 225

OXIDES F R O M

279

MISC.

SECTION 225: -Oxides frcm Miscellaneous Compounds 1. NaOH

2 . AgN03, NaN02

t

NO2

*

Kornblum, N. ; Singh, H.K.;

Kelly, W.J. Chm, (19831,

J Org

b

2. M e 1 Chou, T.

* ; You,

M.

48,

332

CH3S02( C H 2 I 4 i P r

7 4%


-

26, 4495


CHAPTER 16 PREPARATION OF DIFUNCTIONAL COMPOUNDS

-

SECTION 300: Acetylene

iH3 H C-C C H 0A c

T

Co2 ( C O ) 6

-

Acetylene

1. nBuC=C-)3Al, 3h C H 2 C 1 2 , -78 - 0 ° C

2. CAN, acetone

*

e

CH 3 I H C S C C H C r CnBu 5 5%

Padmanabhan, S . : Nicholas, K.M. Tetrahedron Lett, (19831,

PhCH=C

\

-

Ph(Ph2PCH2CH2PPh2)2 Br

P h H , C O , 5N N a O H t

B n N E t 3 C1

-

* H.

*

2,2239

F I CmC -CSCPh

Galamb, V.: Gopal, M.; Alper, Organometallics, (1983

54%

,2, 801

1. nBuLi 2. Z n C 1 2 3. ICH=CHCl, THF 4. N a N H 2 / N H

Negishi,

* E. ; Okukado,

3(1)

67%

N.: Lovich, S.F.; Luo, F.T. -J Org Chem, (1984), 9, 2629

SECTION 301

-

ACETYLENE

OT f

tB U

I

CH C S C = C HC H

55"C,

*

30 m i n

281

*

C H C S C - C E C CH

Pd(PPh,), CH3cCH2C1, 0

, CuI NEt3,

t PhH

n B u C S C - C E C n-B u -

Rossi, R.; Carpita, A.; Bigelli, C. Tetrahedron Lett, (19851, SECTION 301: Acetylene

-

MeCN

2. Me-C=C-SiMe3

TiC14, 3 . HOH J e l l a l , A.; Zahra, J . - P . ;

*

CH2C12

(fH2)lO CECH

*

*

EtNH2

*

2. I C G C ( C H ~ ) ~ M M ~ ,e O H / E t 2 0 NH20H *HC1 36%

Singh, A. ; Schnur, J.M.

26, 523

0 ye II M e C % CH C C N Me 55%

Santelli, M. Tetrahedron E, (1983),

1 . a q . KOH, C u C 1 , E t N H O H mHC1

CZCH I

54%

CarbOXyliC Acid

1 . Cu2CN2, Me2C =CHCC 1

3

85%


Stang, P . J . ; Dixit, V.

nBuC%H -

ACID

Cornnun,

(1986),

2,1395 C H 3 (CH\2 ) 7 C 111 C I

C C 111 /

HOOC ( C H 2 ) 1 0

16,847

282 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6 SECTION 302: Acetylene

-

* : Sugahara,

Kuwajirna, J.

Alcohol, Thiol

2.

89%

S.; Enda, J.

Tetrahedron Lett, (1983),3, 1061

CH2C1 2 . - 7 8 ° C

CH3CZCSiMe3

PCC

* (87% ee)

Johnson, W.S.*; E l l i o t t , R . ; E l l i o t t , J . D .

J Am Chem ----

e>-CH2A1

Soc,

C1 2 ,

RT,

(19831, 105, 2904

Et20

I!

nB u C=C C E t

76%

H

3. K O H , a q . MeOH

0

SECTION 302

OH

>

4h

I

nBuCSCCHEt

78%

*

Giacornelli, G. ; Lardicci, L.; Palla, F.

( 6 4 % ee,

R)

J Org Chem, (19841, 2, 310 --___

1. tBuLi,

THF

OH

-90°C nC6H, 3CH=C=CH2 -

*

2.

ZnC12,

3. EtCHO 4 . H,Of

Zweifel, G. ; Hahn, G, Hahn, G.; Zweifel, G .

3

-74°C

*

Et

/\/cEC

(erythro:threo

H 95% "'gH1 3 = 4:96)

Chem, (1984), 49, 4565 Synthesis, (1983), 833

--J Org

SECTION 302

ACETYLENE

-

ALCOHOL

283

1 . excess EBuLi TH F # O

7

\u;

H

Sayo,

H0"

2 . HOH

HO

H

2)

(98

N.; Shirai, F.;

* Nakai, T. : Kitahara, E. Chem Lett, --

90%

(1984), 255, 259

THF/Hexane, reflux

*

Utimoto, K. ; Lambert, C.: Fukuda, Y. Tetrahedron

v "'CZC, 71 %

s, (1984), 25, 5423

1 . LBuLi

CH C Z C CH

3

2. Ti(OiPr)4, THF 3-

*

O C H O

CH3CSCCH2CH 80%

Furuta, K.; Ishiguro, M.; Haruta, R.: Ikeda, N.; Yamamoto, H. will Chem Soc Jpn, ( 1 984), 3, 2768

---_

t B u C3C - 6

Brown,

1 . EtCHO, pentane 25OC, 15 m i n

2 . HOCH2CH2NH2

*

OH

1

tBuCECCHEt * 83%

* H.C. ; Molander, G.A.; Singh, S.M.; Rocherla, U.S. J Org Chem, (1985), 2, 1577


PhCHO, nBuCGC1

DMF,

OH

CrC12

I

t

2h

25"C,

SECTION 302

nB u C E C C H P h

82%

* Y Takai, K. ; Kuroda, T.; Nakatsukasa, S.; Oshirna, K. ; Nozaki, H. Tetrahedron L e t t , (1985),

0

26, 5585

1 . CH2=C=CHB(0H)*

!I

5

PhCHCH2CCH3

I

8,

sieve,

Et20

*

H & ".'

HO

H OH

2 . H202/NaOH

OH

9 5%

*

(99:l)

Ikeda, N.; Ornori, K.; Yamamoto, H. Tetrahedron Lett, ( 1 9861, 3, 1 1 75

TiC14,

*

CH2C1 -78°C

8 5%

Danheiser, R.L. ; Carini, D.J.; Kwasigroch, C.A. --J Org Chem, (1986), 51, 3870 1 . LiC=CnC

H 6 13

3 . NaOH/H202

I

0 i -Pr

*

*

HO(CH2)5CSCnC6H1 71 %

Brown, H.C. ; Basavaiah, D.; Eihat, N.G. --J Org Chem, (19861, 51, 4518

SECTION 305

-

ACETYLENE

285

AMINE

OH

1 . 2 HCsCCH2Br 2. PhCHO

Pb,

I

Bu4NBr

TMSCl,

PhCHCH=C=CH2 ( 4 )

*

DMF

t

PhfHCH2CsCH ( 1 )

3 . a q . HC1, A c O E t

OH

Tanaka, H.; Hamatani, T.; Yamashita, S.; Torii, S. Chem Lett, (19861, 1461 -SECTION

303: Acetylene -

95%

*

Aldehyde


-

-


Amide

No Additional Examples SECTION

305: Acetylene -

Amine

1. FBuLi PhCSCH

2.

B F 3 * O E t ? , THF,

-78OC

3.

&”,

, -78°C

4.

LiA1H4,

-78

*

Yamaguchi, M. ; Hirao, I.

-

Boche,

I

Me

8 0%


Me2N-S03Me

-Ph

N +C=C

-1OOC

PhCGC-)3CuLi2

* G. ; Bernheim,

>

n

*

2, 1719

P h C E C N Me

83%

M.; Niessner, M.

Angeu Chem Int Ed -, ----

(19831,

22, 53


N-Bn

1 . [PhC=CLi/SF3.0Et2] THF, -78°C - RT

II

H-C-EPr

2. a q . NaOH

Wada, M.; Sakurai, Y.;

* Akiba, K.


-

SECTION 307

NHBn

I

*

nPrCHECPh

60%

Tetrahedron Lett, (1984), 25, 1083 Ester

No Additional Examples SECTION 307: Acetylene

Ph3P=CHSMe Braga, A.L.;

-

Ether, Epoxide, Thioether

0 II 1 . PhCCl, PhH, RT

2. 230"C, 0.005 mmHg

*

* Comasseto, J.V. : Petragnani, N.


t

25,

11 11

*

2 . [ L i C z C n C 5 H , /Et2A1 C1 ] 8 0 ° C , 2h

* ; Martin, S.J.

49%

-

1 . MeS-SMe2 BF4 RT, DCE, 15 min

Trost, B.M.

P h C=C S M e

J Am Chem ----

Soc,

88%

(1984), 106,4263

SECTION 308

-

ACETYLENE

0 I1

1. 2.

nBuCECCCH3 -

"'+m

HO

TsOH,

OH'

Dibal-H, O"C,

287

ETHER

"'on"

Py

CH2C12

t

l h

,,,-BusG

A

90%

3. a q . HC1, 0°C

-: S- = 9 6 : 4 ) (R

*

Ishihara, K.; Mori, A.; Arai, I.: Yamamoto, H. Tetrahedron Lett, (1986),2, 983 1. PBr3, H C E C C H 2B r

THF

Py,

t

2 . BnOCH2C1, A1

BnOCH2CH2CECH

53%

TH F

Bull Chem Soc Fr, (19861,I1245

Guedin-Vuong, D.; Nakatani; Y. SECTION 308: Acetylene

-

Halide

0

1 . P(OEt3)3

II

2 . CBuLi,

CF3C F2C F 2 C C l

*

CuI

3. T B A F , THF

C F3C F2CsCH

RT

89%

Ishihara, T. ; Maekawa, T.: Ando, T.

-


1 . 12'

C H 3 C H = C =CHHg I

t

-40°C

2 . 3M N a 2 S 2 0 3

3 . 1N HC1

* Larock, R.C. ; Chow, M.-S.

I

I

h

c

CH3C HC Z CH 85%

Organmtallics, (19861,2, 603


-

309: Acetylene SECTION -

Ketone 0

cC6H13 C S C S i M e 3 -

1

CH 3

Kawanami, Y.;

nPrCHCC=CnC6H1

- 1

2 AgBF4, CH2C12 RT, 3 0 m i n K a b u k i , T.; Yarnaguchi, M.

*

THF,

2 . BF3*OEt;,

C=CH

-78°C

3 . A c ~ O , THF,

* ; Rocherla,

U.S.;

Chem Lett, (19831, 35

n II

+ C H ( C H ) 5C=C C C H 72%

Singh, S.M.


BH-HC1 4 M e 2

2 . LiC=CnBu,

-78°C-RT

*

3 . NaOH/H202

* ; Bhat,

CsCCPh

-78°C

B B r 3 /p e n t a n e

Brown, H.C.

II

84%

1 . E B u L i , THF, - 7 8 ° C 2 . B F 3 * O E t 2 , -78°C

1.

nB u C E C B r

"C5H1

-78OC

*

( c H ) C=C H

0

t

Yamaguchi, M. ; Waseda, T.; Hirao, I.

Brown, H.C.

91 %

-78°C

3 . PhCNMePh, THF

!

cH

Me

Tetrahedn>n Lett, (19831, 2, 5131

1. nBuLi, nC 5 H 1

II

t

nPrCHCSEt

SECTION 309

-

62%

N.G. ; Basavaiah, D.

--Israel J

0 nBuCECCCH2nBu II

Chem, *I(

S thesis, (19831, 885 .72

SECTION 311

ACETYLENE - OLEFIN

1 . E B u L i , CH2C12, -78°C 2 . VC13, CH2C12, -78°C

n B u CECH

3. P h C H O , - 7 8 ° C

-

289

0

II

reflux

*

nB u C f C C P h

71 % * Hirao, T. ; Misu, D.; Agawa, T. Tetrahedron Lett, (1986), 3, 933

-


-

Nitrile

No Additional Examples SECTION 31 1 : Acetylene

-

CGC(CH2)90THP

1

C?CSiMe3

-

Olefin

1 . Li(A1HiBu2nBu) DME/hexane,25"C 2 . 3N HC1

THPO(CH2)9CH=CH I 3 . KF.2H20, D M F n C H C S C - 3- .7 4. n B u L i , h e x a n e / d i g l y m e nC H B r 81 % - 3 7

>

Miller, J.A.; Zweifel, C.

e2

B CH = CHnB u

(L)

*

__-J Am Chem Soc,

1 . aq. NaOH, THF 0°C

> -nBuCECCH=CHn-Bu

2 . Cu(acac)2 3. B r C Z C n B u , - 1 5 ° C

Hoshi, M.; Masuda, Y.;

9, 1383

(19831,

* Arase, A. --will Chem Soc @,

(L)

75% (1983),

56,

2855


SECTION 311

1. 2 CBuLi, Et20 -78 - - 4 5 ° C M e 0 CH C S C H O M e

Koshino, J.;

C s TMS

I

CECnC

H 6 13

(_?.C7H1 5 ) 3 B y T H F

-7 8 o c-RT

3 . AcOH, RT, 4 . 3N NaOH

nC7H1 5CSCCH=CH 2 88%

2h

* Sugawara, T.; Suzuki, A .

sy" Commun, (19841,

1 . DBE,

Zn,

EtOH

*

2 . NaOH, MeOH

Aerssens, M.H.P.J.;

I nC6H1 3CH=CH

JCS Chem Comn, (1984), 735

CH = C H CH =C H CH~(CH~)~CSCH t RuH2(PBu3)4 P h H , 8O"C, 2 h

Watanabe, H.; Watanabe, Y.

HCZC

70%

* Brandsma, L.

* Mitsudo, T. ; Nakagawa, Y.i

2,245

C H 3 ( C H 2 ) 5 C = "-L CH = C H E t

88%

Watanabe, K.; Hori, Y.; Misawa, H.;

J Org .-Chem, -

(19851,

50, 565

1 . E B u L i , nC6H13Br 2 . Et2A1C=CnC 5H1 1 Me2C=CHCH2S02Ph

DCE,

AlC1,

t J

Et20, r e f l u x

Trost, B.M.

* ; Ghadiri, M.R.

---J Am Chem

HCCHC=CnC5H1

I

IICgH13 Sot, (1986),

71%

108,1098

SECTION 31 2

-

ACID

-

-

SECTION 312: carboxylic

1 . 2 LDA,

2.

carboxylic

THF

-78°C

nBuCH2C02H

-

1 2 , THF,

*

29 1

ACID

nB uCH C O O H

RT

-- 1

>

nBuCHCOOH

-65°C-RT

overnight

Belletire, J.L. ; Spletzer, E.G.; Pinhas, A.R. Tetrahedron Lett, (19841, 1.

02'

MeCN,

-

82%

25, 5969

10°C

9,w-d i c y a n o a n t h r a c e n e

*

Ph-Ph 2. H202

88%

*

Schaap, A.P. ; Siddiqui, S.; Prasad, G.; Palomino, E.; Sandison,

M.


R

1 . C12CHCC1,

NEt3

2 . E B u L i , THF,

3 . Ac20,

-78'C

4. NaI04, CC14, 5 . aq.

6.

5,2229

Ru02,

-78°C

-

RT MeCN

HOH

NaOH

aq. H

82%

-I

*

Depres, J.-P.; Coelho, F.; Greene, A.E. -J Org Chem, (19851,

50,

1972


--

SECTION 313: Carboxylic Acid

3

Q

1. 0-NS-CN, 2. He,

SECTION 313

Alcohol, Thiol

0°C

*

Ni(R)

QCYOH

3 . H5106

4 5%

t

J Org

Kozikowski, A.P. ; Adamczyk, M.

Chem, (1983),

48,

366

1 . CH2=CHPh

+ -

H2, N i ( R ) A 1 C 1 3 , a q . MeOH

2.

3. NaI04, 4 . CH2N2

Ph H

H O O C G OH

NaHC03

90%

(_R : _S = 1 : 1 ) Kozikowski, A.P.*; Kitagawa, Y.; Springer, J.P. JCS Chem C a m , (19831, 1460 ---

b

5.76

NaOH,

1 5 mmol Cu, 0 . 6 6 CC14,

t

Sasson, Y. ; Razintsky, M.

"'fY O Y O fic8H1 7

2 3 0 . 4 9 HOH

1 . TiC14,

80°C 6h

2. 3.

CF3COOH *HOH Jone's Oxidation

4.

KOH/HOH

COOH

87%

JCS Chem Comn, (1985), ---

CH2C12

* Elliott, J..D. ; Steele, J.:

>

nC H -

1134

" Y C O O H

H

Johnson, W.S. Tetrahedron Lett, ( 1 9851,

OH

7 6%

26, 2535

SECTION 313

ACID

- ALCOHOL

1. nBuLi,

oc CP

\ /

F(

e,,#,

'%

THF,

2 . Et2A1C1,

PPh3

3.

cc II

4.

EtCHO,

293

-78OC

-40°C ti Me

-10°C

>

2 CBuLi

HOOc%Et H0 ""'

5. M e 1

0

6. oxidation

no y i e l d

*

Davies, S.G. ; Dordor-Hedgecock, I . M . ; Warner, P . ; Ambler, P.W. Tetrahedron Lett, (19851, 26, 2125, 2129 * Davies. S.G. : Dordor. I . M . : Walker. J.C.: Warner. P. * ' Tetrahedron Lett; ( 1 984) 3, 2709 Davies. S.G. : Dordor.. I.M.: Warner. P. --J& Chem &, (1984), 956

-

cp

,

1

1 . LDA

1/ c c H 3 ",,,

Ph,P J

2.

MX

_______)

ti o

;

HO ,$Et

E t $OH

, c A H

" 0 2 C d H

3. EtCHO

"%,

4. o x i d a t i o n F1X

=

MX

= SnC12

iBu2A1C1

*

(5.2 (1

:

Liebeskind, L.S. ; Welker, M.E. Tetrahedron Lett, ( 1 9841,

1)

73%

11 . 6 )

66%

3, 4341

* 91 % Chong, J.M.: Sharpless, K.B. Tetrahedron -Lett, (19851, 26, 4683


Lo3:h

1 . KN(TMS)2,

Me

SECTION 314

TMSCl

2 . CH2N2

0

3.

L 5 i

KOH,

4. H2,

Pd-C,

"o Vi'% z c ~Me oH

t

MeOH MeOH

82% (2S,3R

1 . PhCHO, CsF,

HO

THF

reflux

C H 3 C H C 0 2 S i M e 3 o____L__)p

I

SiMe3

h

v

z

HO H ph/\/'OzH

Me

2 . H30t

(74

-

I

C H C H CCH2C02Me 3 21 Me

PLE 1M p h o s p h a t e

(2)

t

ke 26)

:

Bellasoued, M.; D u b o i s , J.-E.; Bertounesque, E. Tetrahedron Lett, (1986), OH

2,1152

J Org C h m , (1986),

Y

Kallmerten, J . ; GoUld, T . J .

= major)

84%

3, 2623 OH I

C H 3 C H 2 1CCH2COOH Me 51 %

(2)

3d

PLE = P i g L i v e r E s t e r a s e

Wilsgn, W.K.; Baca, S.B.; Barber, Y.J.; Scallen, T . J . ; horrow, m

.

L.J.

--J Org Chere, (1983),

SECTION 314: Carboxylic

Acid -

Aldehyde


48,

3960

ACID

SECTION 31 5

SECTION 315: Carboxylic

-

Acid -

295

AMIDE

Amide

c::-

1 . ~ B U O ~ C N) E~t 3 ~ ,

sd

DMAP, 25"C, 8 h

Flynn, D.L.;

H

t 2 . 3 L i O H , a q . THF RT * Zelle, R . E . ; Grieco, P.A. J Org Chem, (1983), 48, 2424

B 0C

96%

-

-

1 . 3 BnO2CNH2, 6 N E t 3 3 NCS, MeOH, 0 ° C 2 . 0 3 , CH2C12/MeOH, - 7 8 ° C

tt0I

3 . Me2S, - 7 8

Me

-

NH-CBZ 40%

25°C

4 . Cr03, a q . H2S04

(79% ee) acetone Fitzner, J.N.; Shea, R . G . ; Fankhauser, J . E . ; Hopkins, P.B. -J Org Chem, (19851, 50, 419 m\ l \- N a t , 2.

L)NCPh,

1

P h2CH COOH

-15"C-RT,

3. HS

Stamm, H. 0

* : Weiss,

0

" A0 BnC-N

U

B n +''

Evans, D.A.

R.

THF Id

*

Ph

I

PhCNHCH CH CCOOH

21

Ph

58 %


1 . L D A , THF, - 7 8 ° C 2. B O C - N = N - B O C

Bn-CH-COOH I

t

3 . g l . AcOH

4 . L - i O H , a q . THF

* ; Britton,

19

T.C.;

*

N-BOC I

NH-BOC

(99% ee)

Dorow, R . L . ;

7 5%

Dellaria, J . F . 6395

J Am Chem Soc, (19861, ----

108,


1. nBuLi

0

2.

Bn-CH-COOH

Id

PhCCl

I

Trimble, L.A.;

y-BOC NH-BOC

*

3 . LDA i -Pr

SECTION 316

4 . BOC-N=N-BOC 85% 5. LiSH (R:S = 17:83) 6 . AcOOH * Vederas, J . C . ---J Am Chan Soc, (1986),

108,6397

Related Methods: Acid-mine (Section 31 6) hide-Ester (Section 344) mine-Ester (Section 351

SECTION 316: Carboxylic Acid - Amine 1 . BnNH2,

4A s i e v e

2 . TMS-CN,

CH2C12

C H 3 C H = C H C H 0 3 . 6N H C 1 ,

reflux

4.

Greenlee, W.J.

COOH

I

*

CH 3CH = C H C H NHB n

Dowex 50W-X4 HOHIPyIMeOH

43%

J Or& Chan, (19841, 49, 2632

-

)I

1 . EtOH,

H2NT:

Me2NH,

2 . LBuCHO,

3. PhC02)0, 4.

CH3

LDA,

RT

pentane

THF,

30°C -78

B r CH e

COOH

- 0 ° C *cH3+NH2 O

M

e

62

OMe HO \ / 6N H C 1 , 1 8 5 ° C Dowex 50W-X8(Ht) HO 43% )t Seebach, D. ; Aebi, J . D . ; Naef, I?.; Weber, T. Helv Chim Acta, (1985), 144 5. 6.

---

68,

C02Et

Ph2C=N

OA c

O'Connell,

P h - B a

,

tBu

1

2.

HC1-Et20

3.

6M H C 1 ,

* M.J. ; Falmagne,

297

AMINE

d : ' K t ,

1.

\

-

ACID

SECTION 31 6

THF,

0°C

31%

JCS Chem Comn, (19851, 1168

J.-B.

2. MeI,

( MeS ) 2 C = N C H 2 ! - N 3

3/

< OMOM

1

PhCHCOOH

heat

1 . LDA. THF.

,OMOM

o d

NH 2

*

-78

-78°C

-

1 N HC1

Me

-20°C

*

\

H2NCHCOOH 82%

*

(95% eel Ikegami, S.; Hayama, T . ; Katsuki, T. ; Yamaguchi, M.

-


e x c e s s Et2NH

P

O

O

H

RT,

Chow, J.M.; Sharpless, K.B.

02CCH=CHMe

OOH

4h

1.5 Ti(OiPr)4

.r\_C7H15

* -J org

OH NEt,

(20

1.

EtCU.BF3

2.

LDA,

3.

NaN3

4.

Ti(OBn)4

,

1)

92%

50,

(19851,

TMSCl,

Et

5 . H2/Pd

Oppolzer, W.*;

3, 3403

1560

97.8% ee

99.3% ee 37%

Pedrosa, R . ; Moretti, R.

Tetrahedron E ,(1986),

3, 831


1 . NBS, P

h

d

CBZ

CC14,

reflux

2 . CH2=C: O E t OSiMe2tBu

4

o

ZnC12,

+

*

THF

3 .HOH

4.

H2/PdC12,

,

20 psi

SECTION 316

3

XHO 2 CH 2 C 0 2 E t

EtOH 25°C

71 %

(97% ee)

*

Sinclair, P.J.; Zhai, D.: Reibenspies, J.: killiams, R.M. 108, 1103 J Am Chem Soc, (1986), ---1. PhCHO

(TMS)2NCH=C(OTMS)2 Me3SiOTf,

2. H30

-78"C,

H ; 2

3h

t

t

PhCHCHCOOH I

OH

95%

(threo:erythro

= 2 : l )

*

Hvidt, T.; Martin, O.R.; Szarek, W.A. Tetrahedron Lett, ( 1 986),

3, 3807

1 . BOC-N=N-BOC

phro H J

TiC14,

CH2C12,

2 . CF3COOH,

Me&NMe, OTMS H

3.

LiOH

4.

D o w e x 50W

5. H2/Pt02

6.

Gennari, C.

* : Colombo,

D o w e x 50W

-78°C

RT 50% (98% ee R)

L.: Bertolini, G. J Am Chem Soc, (19861, 108, 6394 ----

SECTION 317

ACID

-

ESTER

299

1 . [Au(Cy-NC),]+BF4-

c a t . , Me02CCH2NC

PhCHO

2 . c o n c . HCl/MeOH,

50°C

3 . 6 N HC1, 8 0 ° C , 6h cat. =

t

90%

@ + NPPh, 5Ntt2

PPh,

Ito,

HO *COOH Ph NH,*HCI

* Y. ; Sawamura, M.;

*

Hayashi, T. J Am Chem Soc, (19861, ----

108,6405

Related Methods: Acid-hide (Section 31 5) hide-Ester (Section 344) Amine-Ester (Section 351

-

SETION 317: Carboxylic Acid * Ester COOH

NaN02/aq. H2S04 t

R T , 15h 70%

Gringore, O.H.;

Rouessac, F.P.

63,121

Org Syn, (19841,

NaIO4-RuO4.2H20 CC1 4 - H O H , 1 Oh

nB u

*

t

Torii, S. ; Inokuchi, T.; Kondo, K. --J Org Chem, (19851,

nBu

93%

50,

4980


SECTION 318

C02Me

+

CCOOH

CH2N2

quant.

* Ogawa, H.; Chihara, T.; Taya, K.

---J Am Chem Soc,

PLE,

nBu$,C02Me

C02Fle

pH 8 ,

0.1N

(19851,

107, 1365

NaOH t n B u T. C02H

phosphate

C02Me

( R-: S- = 2 5 : 7 5 ) PLE = P i g * L i v e r E s t e r a s e Schneider, M. ; Engel, N.; Boensmann, H. Angw Chem Int Ed h g l , (19841, 23, 66 CH2C02Me CH2C02Me

PLE, aq.

pH 7

*

KH2P04

H-7,

CH2C02Me

( 7 9 ~e e

PLE = P i g L i v e r E s t e r a s e

CH,COOH

* Jones, J.B.

~f

95%

Lam, L.K.P.; Hui, R.A.H.F.; -J Org Chem, (1986), .-51, 2047 SECTION

- Ether,

318: Carboxylic

Epoxide, Thioether

1 . Na2W04.2H20, n P r C H =CHCOOH

HOH, 2 . aq.

1N K O H ,

3h

0 65OC / \ t nPrCH-CHCOOH

PH 6 H202(pH 5.8-6.8)

*

Kirshenbaum, K.S.; Sharpless, K.B. -J Org Chem, (19851,

50,

82%

1979

SECTION 319

ACID

-

HALIDE

1 . NaHC03, a q . a c e t o n e

2 . K H S 0 5 , Na2EDTA

PhCH=CHCOOH

>

27"C, 2h 3 . a q . HCI

*

Corey, P.F. ; Ward, F.E.

PhCH-CHCOOH 92%

-J Org

Chem, (1986),

1 . 2 L D A , THF/HMPA -78OC

PhCH2COOH

0

/ \

2 . BrCH2SeBn, l h -78OC RT

51, 1925 CH2SeBn

>

I

PhCHCOOH

-

81 %

* Reich, H.J. ; Jasperse, C.P.; Renga, J.M. -J Org e, (19861, 2,2981 SECTION 319: Carboxylic Acid

- Halide, Sulfonate

C 1 2 , C1S03H

C H 3 ( C H 2 l 1 6COOH

TCNQ, 15OOC

*

c1

I

CH3(CH2)1 5CHCOOH 88%

TCNQ = 7 , 7 , 8 , 8 - t e t r a c y a n o q u i n o d i r n e t h a n e

Crawford, R.J.

* -J Org Chem,

(1983),

48,

1364

1 . M e M g I , THF

ref1 ux

H C Z C C 0OH

2 . AcOH

*

>

ICH=CHCOOH

(I)

80%

Jung, M.E. ; Hagenak, J.A.: Long-Mei, Z. Tetrahedron -.Lett, (19831,

2, 3973


Br

NaN02, K B r i PrCHCOOH

SECTION 320

>

H F/ PY

I

iPrCHCOOH 84%

Shih, J.; Surya Prakash, G.K. Helv Chim Acta, (19831,

Olah, G.A.;

---

12,

CH3COOH

CU(OAC)~

>

r e f l u x , 40h

Horiuchi, C.A.

* : Satoh,

1028

ICH2COOH 80%

-Chem Lett,

J.Y.

66,

(19841, 1509 Br

0

It

1 . LiA1H4

P h 2 A s CH C O O H

I

nBu -

2. Br2

* T. ; Joussen,

KauffmaM,

t

I

nBuCHCOOH

56% R.; Woltermann, A. Chem Ber, (1986), 119,2135

7 -


-

Ketone 0 II

S

1 . PhCCH,,

K

3

BrHgO2CNUN

150°C

COZMgBr 2 . H30

4 eq.

*

DMSO

0

II

PhCCH2COOH

t

74%

*

Matsumura, N . ; Asai, N.; Yoneda, S. JCS Qleol Cam, (1983), 1487

---

SECTION 320

ACID

-

303

KETONE

H O H / MeOH Me0

Kunz,

COOH

* H. ; Lindig,

I1

*

PhCCH2CH2COOH

7OoC, 3 0 m i n

Chem Ber, (1983),

M.

1 . 2 LDA, THF, 2 . HMPT,

CH3(CH2)4COOH

0

RT,

-

116,220

-50°C nBu

It -1

*

CH3CCH2CHCOOH

0°C

65%

4 . a q . H C 1 , RT,

overnight

Miyashita, M.; Yamaguchi, R. ; Yoshikoshi, A. J Org C h a , (1984),

-

0

30 m i n

3 . CH2=CMeN02, 4 h

-100

quant.

-

*

2, 2857

0 II

OSiMe,

1 . MeCH-CHCCN, CH2C12,

-70

TiC14

-

-30°C

*

2 . HOH

65%

El-Abed, D.; Jellal, A.; Santelli, M. Tetrahedron 0

II

PhCH=CHCCH3

e

-

,

C02,

*

E, ( 1 984), 25, 4503

MeCN

COOH 0

w-

I

II

PhCHCH 2 C C H

Hg e l e c t r o d e s Et4NtC104-

* A . ; Sasaki, K.

Harada, J.; Sakakibara, Y.; Kunai, Bull chem Soc

--- e, (19841,

82%

57,

611


SECTION 320

0

l o 2 , MeOH, 4 0 ° C h 7

Rose B e n g a l ,

4h 91 %

Utaka, M.;

*

Nakatani, M . ; Takeda, A. Tetrahedron, (19851,

C02TMS

1. LiBr,

I

2 . PhCC1,

:

CH2

I

C02TMS

Et20, O"C,

NEt3

0

it

l h

3 . a q . NaHC03

4.

2, 2163

*

PhCCH2COOH

88%

4M H 2 S 0 4 ( p H 2 - 3 )

Rathke, M.W."; Nowak, M.A.

-Syn Conmun,

(1985), 15, 1039

Br

I

PhCHCH3

C O ~ ( C O ) ~ ,C a ( O H ) 2 tBuOH,

1 atm. CO 25"C, HOH

t

PhCHCCOOH

J

CH3

72% \

Francalanci, F.; Bencini, E.; Gardano, A.: Vincenti, M.: Foa, M. Chem, ( 1 9861, 301, c027 -J Organomet Review: lISynthesis and Properties of a-Keto-Acidsl1

Cooper, A.J.L.;

Ginos, J . Z . ; Meister, A. Chem Rev, (19831, 83, 321 --

Also via: Ketoesters (Section 360)

SECTION 322

ACID


-

-

OLEFIN

-

Nitrile

305

1. nBuLi 2 . Me1 3. EBuLi

4. E t I 5 . 6 n HC1

'OMOM

6.

Me E t

m

xC02H CN 65%

1 % K C03/MeOH

(R) Hanamoto, T.; Katsuki, T. ; l/?amaguchi,M. Tetrahedron Lett, (1986), 27, 2463 Also

via: Cyanoesters (Section 361

-.SECTION

322: Carboxylic Acid

-

Olefin

MeOH

* Saito, I. ; Nagata, R.;

49%

Yuba, K.; Matsuura, T.


0

1 . LiN(TMS)*,

II

OCEt

2, 1737,

THF

-78°C 2 . t B u M e 2 S iC1

HMPA, 36

Ireland, R.E. ; Varney, M.D.

4439

Me

HozC-

>

-78°C-RT

2 Am

I

S i-LB u \

Me

93%

chem SOC, (1984),

106,3668


SECTION 322

0

II

1 . CH2=CHCSiMe3,

SiMe,

TiC14

CH2C1 2 , - 7 8 ° C 2 . a q . NaOH, THF,

aq.

30% H202

-40°C

49%

Danheiser, R.L.*; Fink, D.M.

26,

Tetrahedron E ,(1985), 1.

0

,

TiC14

2 . L i O H , T H F , HOH

0

2509, 251 3

""'COOH (99.9% ee)

* Helmchen, G.

*D,, , d,,

Poll, T.: Sobczak, A.; Hartmann, H.: Tetrahedron E ,(19851,

a:::";.. MeMgBr,

THF

79%

26, 3095

+

"I'

'I,,

C u B r -Sli;'e2

COOH

OH 2) 97%

-20°C ( 98 * Curran, D.P. ; Chen, M.-H.; Leszczweski, D.; Elliott, R.L.; Rakiewicz, D.M. J Org &em, (19861, 51, 1612 P Ph3

\ /

co

I.

CH2=CH C

II 0

*

, znc12

CH2C12,

Fe

/ \

Q

RT b 7

CP

2.

Davies, S.G. ; Walker, J.C.

CAN,

a q . THF

COOH

( 2t

= major)

JCS Chem Conm, (19861, 609

80%

SECTION 323

ALCOHOL

-

307

ALCOHOL

Also via: Hydroxy acids (Section 313); Olefinic amides (Section

349); Olefinic esters (Section 362); Olefinic nitriles (Section 376).

SECTION 323: A l ~ h o l ,-.Thiol

-

1 . 2 Sm12, PhCHO

2 . H,O

-

-

Alcohols Thiol

OH

0.5 min

I

t

t

PhCHCH Ph

I

*

J

OH

Namy, J.L.:

Souppe, J.; Kagan, H.B. Tetrahedron Lett, (1983), 24, 765

4

Zn ( B H 4 ) 2 &Bu U P

-

B

0

Et20,

*

0°C

*

+ 4

-

B

95%

.

HO

HO (87

:

1 3 ) no y i e l d

Nakata, T. ; Tanaka, T.; Oishi, T. Tetrahedron E ,(19831, 2, 2653

*

Me N H + B ( O A C ) ~ - , AcOH

R -

Me?N, - 2 O o C , 5 h 8 6 % ( a n t i : s m = 96:4) * D.A. : Chapman, K.T. Tetrahedron E,(19861, 3, 5939

iPr

Evans,

FR

R = Ph

1. Dibal-H,

*

2.

THF

1 0 % HC1

87%

(un:anti

=

93:7)

Kiyooka, S. ; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett, (1986), 3, 3009

R

= Me

Anwar, S.;

1 . iPr2SiHC1,

Py,

PhH

2 . SnC14, CH2C12, - 8 0 ° C 61 % 3 . a q s HF, MeCN Davis, A.P. JCS Chem Corn, (19861, 831


u"

Ph Br

O*Si /J

/ \

Nishiyama,

1 . nBu3SnH, AIBN PhH, reflux

---n + APh /Ph

*

2 . 30% H202, K F D M F , 6 0 " C , 8h

* H. ; Katajima,

SECTION 323

HO OH (84

HO

OH

16)

85%

T.; Matsumoto, M.; Itoh, K. (19841, 9, 2298

J Org Chat, ---

a

1. nBuLi 2'

3. E t C B n

'd

Li

, THF, -78°C

Et

b r

* D.

(SR:SS

Nijera, C.; Yus, M.; Seebach, Helv Chim Acta, (1984), ---

55% = 1:l)

3, 289

( e r y t h r o : t h r e o = 4:l) * Pelter, A. ; Bugden, G.: Rosser, R. Tetrahedmn Lett, (1985), 26, 5097

SECTION 323

ALCOHOL

ALCOHOL

a na p i

309

I

CH3CHCH2NEt2

Papini, A , ; Fiorenza, M.; Ricci, A . Tetrahedron ( 1 9831,

s,

55%

24,

231 1


'3-0 ,

DCE

ts

TFA,

reflux,

*

I d

@OH

64% Tetrahedron E,(1983), 2, 3051

SiMe, CO,Me

Chan, T.H.;

SECTION 326

Kang, G.J.

1 . MeOH/HOH, r e f l u x 2. A m b e r l y s t A26 MeOH , R T - r e f 1 u x

O y N 3.

CCI,

6F1 HC1

HO t

e H ; : , + -

OH

86%

*

C a r d i l l o , G. ; Orena, M.:

Sandri, S. JCS Chem -.Carm, (19831, 1489

--

1 . TsNCl -Nat .3H20

1 % Os04, 60°C, 2.

Herranz, E.;

CHC13/HOH

BnNEt3C1

Na2S03,

81%

reflux

* Sharpless, K.B.

Org Syn, (1983),

2 CH2=CHCH=CH2, Pd(acac)2,

t

0.5

80°C PPh3

* ~C5Hll

autoclave

Groult, A . : Guy, A .

61,85


98%

2,1543

NH

ALCOHOL

SECTION 326

/ 0 \

-

AMINE

,

1. Me3Sn-N3

PhCH-CH2

reflux, 2,

Fiorenza, M.;

CH2C12

*

16h

Ph&OH

H02CCH C 0 2 H , E t 2 0 r e f l u x , 2h Ricci, A. ; Taddei, M.; Tassi, D. Synthesis, (1 9831, 640

*

r e f 1ux

*

315

2.

83%

(96

LiA1H(OMe)3, NaOMe, E t 2 0

92%

O°C

4)

Narasaka, K. ; Ukaji, Y . ; Yamazaki, S. Bull Chem Soc J , (19861, 59, 525 --* Chem Ftt, ($41, 147 Narasaka, K . ; Ukaji, Y . Narasaka, K . ; Yamazaki, S.; Ukaji, Y . Chem Lett, (19841, 2065

Jacquesy, J.-C.; Jouannetaud, M.-P.;

Tetrahedron

0 A,NMe* Ph A Me

Morellet, G.; Vidal, Y .

E,(19841, 25, 1479 HO

PhMe2SiH, TBAF,

>

phOyNMe* Me 8 3 %

HMPA 12h

Fujita, M . ; Hiyama, T.

RT

* -J Am .-Chem Soc,

(threo:erythro

(19841,

106, 4629

= 99:l)


CH2=C

/

1 . Ph-NZO,

OTMS

PhH

2O0C

*

SECTION 326

OH

I

PhCHCH2NHPh

2. LiA1H4, E t 2 0 78% * Sasaki, T.; Mori, K.; Ohno, M. Synthesis, (19851, 280 h

P‘

0 EtCH-CHCH20H / \

e x c e s s Et2NH RT, 5 h _______)

1 .5 T i ( O i P r ) 4

*

Caron, M. ; Sharpless, K.B.

OH NEt

E t A . p c 3 I - l

OH

Et+OH

+

NEt,

1 )

(20

90%

J Org Chm, (19851,

3, 1557 ~-Bu

0

Overman, L.E.

*

; Lesuisse, D. Tetrahedron Lett, (1985), 1 . TMS-CN, Zn12,

C H ,LC l , 12h

2 . HCl/MeOH 3 . N a O H , HOH

Cassman,

* P.G. ; Haberman,

L

*

91 %

26,

4167

c:* 61 %

L.M. Tetrahedron Lett, (19851,

-

26,

4971

SECTION 326

-

ALCOHOL

317

AMINE

HO Ph

1 . PhMgBr, Et20

CN I

CH3COSiMe3

RT

CH3

2 . NaBH4, MeOH RT

I

*

I 1

CH C -CHNH

rn

I

CH3

*

84 1

Krepski, L.R. ; Jensen, K.M.; Heilmann, S.M. ; Rasmussen, J.K. synthesis, (19861, 301 NHTMS / 0\

PhbHCH3

Ph CH- CH

(R)

(2),

65OC

H OHH

2-y;

>

Ph

H

44h

80%

*

Atkins, R.K.; Frazier, J.; Moore, L.L.; Weigel, L.O. Tetrahedron Lett, (19861, 3,2451

4

SiMe,

n B u N H 2 * T F A , 35°C HOH,

48h

37% aq. HCHO

Larsen, S.D.; Grieco, P.A.*; Fobare, W.F. ---J Am Chem Soc, (19861, 1 . (-) I

IpC2BH, -15OC

2 . NaOH/HOH

t I

Bn

Bn

IpC2BH = i s o p i n o c a m p h e n y l b o r a n e

Brown, H.C.

108,3512

* ; Prasad,

94%

(84% e e )

J.V.N.V.; Gupta, A.K. -J Org Chem, (19861,

51,

4296

89%


SECTION

RU

327: Alcd.lol,

O

R

"hi01

-

Ester

'

*

R = CH2CH=CMe2 R ' = Me'

R

O R'

M

Baker's Yeast, MgS04 D-glucose, KH2P04, H O H

*

*

SECTION 327

7 3%

(92% ee)

Hirama, M. ; Shimizu, M.; Iwashita, M. JCS Chem Coma, (19831, 599 Thermoanaerobium brockii R = Et 80% Trypton, Na2S, y e a s t extract R' = E t (84% ee S ) D-g1 u c o s e * Seebach, D. ; Ziisr, M.F.: Giovannini, F.; Sonnleitner, B.: Fieehter, A. ,mewChem Int Ed R q l , (19841, 23, 151 R = Me Baker's Yeast, HOH E' = Et s u c r o s e , 30°C (S:! = 93:7) -7-

*

Seebach, D. ; Sutler, M.A.; Weber, R.H.; Ziiger, M.F. Org Syn, (19841, 63, 1 Seebach, D * ; Giovannini , F ; Lamatsch, B. Helv Chim Acta, (1985), 68, 958

.

.

---

LiBH4, L B u O H , THF 94% (RR')NN'dibenzoyl (87% ee R) * cystine, -78 - - 3 O O C Soai, K. ; Yamanoi, T.; Hikima, H.: Oyamada, H. JCS Chem Coma, (1985), 138 ---

R = Ph R' = Et

*

0

V-Sn

Bu,

H CIIC 0 2 B u

, w oMe2 B u

CH,C1

HO (80

L

*

L

,&CO,Bu Me

+ 20)

90%

Yamamoto, Y. ; Maeda, N.; Maruyama, K. JCS Chem Coma, (1983), 774 7 -

SECTION 327

-

ALCOHOL

BrCH2C02Et,

ESTER

0°C

319

c O,Et

>

Z n - g r a p h it e

Boldrini, G.P.; gavoia, D.; Tagliavini, E.; Trombini, C.*; Umani-Ronchi, A. -J Org Chem, (1983), 48, 4108

coi

P h C H 2CH 2 C H 0

OH

P ,r 0 - 2 o o c

C1 3Ti'

88%

I

BnCH2CHCH2CH2C02iPr

C H 2 C 1 2 , 2h 80% * J Am Chem Soc, (19831, 105, 651 Nakamura, E.; Kuwajima, I. ----

,0SiMe2tBu

Me

PhXCHO

2 . 8 C H = C 'OMe

Me

* Ph*CO,Me

t Ph&C02Me

OH

CH2C12, B F 3 * 0 E t 2 HO -78"C, 4h (15 : 1) * 81 % Heathcock, C.H. ; Flippin, L.A. J Am Chem Soc, (19831, 105, 1667 ----

THF,

-78°C

( 9 2 % ee S )

X:&070 K+

G i # O

80%

O&

H * Brown, H.C. ; Cho, B.T.: Park, W.S.

--J Org

= K9-DIPGF9-BBNH

Chem, (1986), 51, 3396


a v 0

0

II

>

CH,

PhCC02Et

SnCl 2 / D i b a l -H,

Mukaiyama,

T.;

-1

C H 30 IIC C 0 2 E t

G.G.;

(19851, 813, 1359

0

OH

I

CH3CHC02Et 81 %

( 8 9 % ee S ) Jadhav, P - K . J Am cfe im Soc, (1984), 1531 ----

106,

OH

S iMe3

I

TBAF

D(

C02Me

C02Me

* ; Blankenship,

Wells, G.J. J Am Chem Soc, (19841, ----

1 . L I C A , THF -8OOC

II

R*OCCH3

R*

[XCHCH3

>

CH 3CH0

Paquette, L.A.

0

90%

24h

O O C ,

* ; Pai,

*

(85% ee S )

P

-Chem Lett,

OH PhtHCO2Et

O O O C

20 rnin Tomimori, K . ; Oriyama, T.

o ,

Brown, H.C.

CH2C12

SECTION 327

106,6442

RO-Et

9

F

3.

*

90%

+

+H!:ri z

C.;

HO

0 (93

:

EtCHO, TiC14 CH2C1

- Ar

HO 7) 67%

A r :I@

I

Helrnchen , G. ; Lei kauf , U. ; Taufer-Knbpf e l , I. Angew C h a Int Ed Engl, (1985),

---

2, 874

ALCOHOL - E S T E R

SECTION 327

n Ho

0

OH

CH2C12, N E t 3 ,

*

K i m , S . ; Chang, H.;

Wulff, W.D.

K i m , W.J.

Soc, (1985),

'd

Zr(acac)4y

I

CH3CH(CH2)40Ac

60h

Hirobe, M.

94%

*

Tetrahedron Lett, (1985) , 26, 1977

1 . CH2=C; -195

,SL i

-

2 . H30t

SEt

THF/Et20

-120°C

Ph

Me

Me

COSEt

OH (96

OH

50%

Meyers, A . I .

107, 503

OH

t

Kunieda, T. ; Mori, T.; Higuchi; T.;

PhCHCHO

HO

P N A c

I

*

o y P h 0 93% J Org Chem, (19851, 50, 1751 Id

J Am Chem ----

S.R.

CH2C1

CH3CH(CH2)40H

n

73%

* ; Gilbertson,

OH

t

321

* ; Walkup,

R.D.


4);

2,5089


SECTION 327

1. 2 LiNEt2

OH

I

THF/HMPA

CH3CH(CH2)3C02tB~

-100

-

Me

t

-78°C

2 . Me2S04

Me

- 1 00°C

-Chem Lett,

Narasaka, K . ; Ukaji, Y.

HO

HO OH wPr & c o p

P

0

(8)

71 %

(19861, 81

F e C 1 2 , MeOH

V&CO,Me

(92)

90%

50 p s i H2 18h

(9n:anti = 9:l)

*

Y

Kathawala, F.G.; Prager, B.; Prasad, K . ; Repic, 0.; Shapiro, M . J . ; Stabler, R.S.; Widler, L. Helv Chim Acta, (19861, 69, 803

---

qMS 0

C02Et

%,

TiCl

4 y

-78OC,

Molander, G.A.

* ; Andrews,

SCEt3

Masamune,

* S. ; Sato,

OH C02Et Me

CH2C1

I

> 2h 88%

S.W. Tetrahedron Lett, (19861,

-

3, 3115

82%

pentane

(91 .2% ee R ) -78OC, 6 h T.; K i m , B.M.; Wollmann, T.A. ---J Am Chem Soc, (19861, 8279

108,

-

ALCOHOL

SECTION 327

0

MoOPH,

R * O l C H 2 C H 2Ph

ESTER

323

0

4h

II

>

R*OCCHCH2Ph I

2 KN(TMS)2 8 CH3CH2yHCH3

v

OH

(R:S Gamboni, R.; Tamm, C.

HO 55,

/

H

c H -c' - c o

*

Tetrahedron .-Lett, (1986),

1 . CsSAc, ET

DMF

overnight

2 . 3% H C l / E t O H

= 1:99)

3, 3999

H

*

7 3%

1S H C-' - C 0

%L$

CH

Et

86%

( 9 2 % ee R)

Strijtveen, B.: Kellogg, R.M.

* -J Org Chem,

co *Et

(19861,

51, 3664

- 6.. C02Et

Sm12,

-98OC

TH F / E t O H

* Molander, G.A. ; LaBelle, B.E.: Hahn, G. -J Org Chem, ( 1 9861, 51, Also via: Hydroxyacids (Section 313)

68%

5259


SECTION 328: Alcohol, ,Thiol

--

Me

-


Me

CH =CHCH2TMS

B n - 0 *CHO

SECTION 328

_______)

CH2C1 2 , - 7 8 ° C SnCl

Heathcock,

(35

:

I

4

94%

* C.H. ; Kiyooka,

S.; Blumenkopf, T.A. J 3Chem, (19841, 49, 4214 Kiyooka, S.; Heathcock, CTH. Tetrahedron E ,(1983), 24, 4765

a -R PdC12, CuCl

DMF,

45OC, 02'

T i u s , M.A.

* ; Thurkauf',

HOH,

NaHP04

2.5h

66%

A.

-J Org Chem,

(1983),

48,

3839

tBuOOH, PhH, 6h

"

O

n

A 1 ( O i P r ) 3 , 25OC

*

Takai, K.; Oshima, K. ; Nozaki, H.

80% (E : Z- = 1 3 : 8 7 )

---B u l l Chein Soc Jpn,

(1983), 56, 3791

SECTION 328

ALCOHOL

-

ETHER

- q rh?

0

(A)

)\

Ph Ph

OH

HOdNH-Bn Hw,ti(#JH-Bn

9

0

325

LBUOOH

'h

Ph

(k) T i ( O i P r ) 4 , - 2 O O c Johnson, R.A.;

Lu, L.D.L.;

CH3(CH2)7CH=CHCH20H

(L)

Hanson, R.M.; H i l l , J.G.;

OH

96% e e

F i M , M.G.; Sharpless, K.B. -J w g C h a p .(1984), 728

2,

( + I d ie t hyl t a r t r a t e

*

4 i sieve, - 2 0 0 ~

C H C1

OH

2.4:2

=

*

1 :2.0) 82% e e

0 nC8H17CH-CHCH20H / \

7 9%

-

-

Sharpless, K.g.* 30rFMChem, (1986), 51, 1922 Sharpless, K.B. ; Exon, : Regenye, R . Org S z , (19841, 63, 66

.

1 . BH2C1 - O E t 2 , E t E O lh O'C, 2. N a O H , H 2 0 2 EtOH

Borders, R . J . :

( C O )5Cr=C

,OMe

\

Wulff, W.D.

Bryson, T.A.

CECS iMe3

* : Yang,

1.

*

OTMS

'A

nPrC=CH,

, THF

~

50'C

OMe

2. Si02, a i r D.C.

90%

Chem L e t t , (1984), 9

----J Am Chem

58%

Soc,

(19841,

106,7565


Sm12, T H F , RT

H?5°Bn

t

C1 C H 2 0 B n

*

SECTION 328

57%

Imamto, T. ; Takeyama, T.: Yokoyama, M.

ei 5,3225


6

Men

MeTiCl

Ma

CH2C1

Mori, A.; Maruoka, K.:

Yamamoto, H.

-

*

Me

,+"

H

(R:S

=

HO

4:96)


0.5% P d ( P P h 3 ) 4 ,

THF

P h O H , 10 m i n Deardorff, D.R.

0 SiMe,

0 I

Lee,

* ; Myles,

3, 4421

82%

D.C.; MacFerrin, K.D. Tetrahedron E,(19851,

2 . TiC14

26, 5615 OH

1 . Me3SnCH2CH2CH(OMe)2

* T.V. ; Richardson,

quant.

OMe

64% K.A.

-

Tetrahedron Lett, ( 1 985) I

26,

3629

SECTION 328

ALCOHOL

b

CF3COOH,

0

Ph X

H

327

ETHER

NaBH4

+

P h C H 2 0 C H 2CH 2 0 H

20°C

THF,

Nutaitis, C.F.; Gribble, G.W.

-

83%

*

Org &ep -Proc I n t , (1985),

nBu2Sn0, RT -

0

PhCH-CH2

OMe

OH

I

5h

/ \

17,1 1

*

I

t

PhCHCH20Me

PhCHCH20H

s, (19851, 26, 3219

Otera, J. ; Yoshinaga, Y.; Hirakawa, K. Tetrahedron

1 . NCS,

,,,,t(CH2)3SPh

2. MeLi,

-80°C

CC14 THF

-

RT

*

@SPh

*

Harada, T.; Akiba, E.; Tsujimoto, K.; Oku, A . Tetrahedron E,(19851, 1 . PhCHO, S,

Ph

\

CH 3

1.5h CH2C12

-78°C

CH2C12,

2 . ZnBr2,

CH3CH=C

Et3SiH,

-78 3 . HOH

Takeda, T.* ; Tsuchida,

-

-4O"C,

4h

49%

26, 4483 S P h OH

1

t

1

CH3CHCHCHPh

I

CH3

77%

T.: Nakagawa, I.; Ogawa, S . : Fujiwara, T. Tetrahedron E ,(19851, 26, 5313


'02, iP r C H =CH iP r

(r) W.

hw,

Ti (OiPr)4,

TPP = t e t r a p h e n y l Adam,

TPP,

* : Griesbeck, OH

I

0°C

porphine A.:

(L)

Staab, E.

C-CHCHiPr

Me'

T e t r a h e d r m Lett, (1 9861,

60"C,

/ \

7 5%

(erythro:threo

n B u 2 S n 0 , LBuOOH

CH3CH=CHCHnC6H1

0

Me,

t

CH2C1

SECTION 328

3, 2839 OH

0

I

/ \

CH3CH-CHCHnC6H1

7 5%

6h

Kanemoto, S.: Nonaka, T.; Oshima, K.

(threo:erythro

* : Utimoto,

K. Tetrahedron E ,(19861,

= 4:6)

3,3387

c1 I

PhSCHCH3 PhCHO

,

P

L i I

C r C 1 2 , TMEDA, THF, 6 h

>

25°C

h OH (88

Me

A Ph+

+

OH 12)

96%

Nakatsukasa, S.; Takai, K.*:

Utimoto, K.

-

J Org Chem, (19861, 51, 5045

1. Ti(OiPr)4, C H =C

,CH \

3

-20°C

( + ) d i i s o p r o p y l t a r t r a t e HO Me cumene h y d r o p e r o x i d e P h S A o H

CH20H

3 i sieve

2.

quant.

P(OMe)3

3.PhSH,

KO, S.Y. ; Sharpless, K.B.

= 9:l)

(92% ee)

Ti(OiPr)4

* -J Org Chem,

(19861,

2,5413

SECTION 329

ALCOHOL

-

HALIDE

329

Reviews:

"Chelation or Non-chelation Control in Addition Reactions of Chiral a and 8-Alkoxy Carbonyl Compoundstf Reetz, M.T.

*

Angeu Chem Int Ed Engl, (19841,

23, 556

"Asymmetric Epoxidation of Allylic Alcohols: The Sharpless Reaction" Pfenniger, A.

*


SECTION 329: Alcohol, mi01

-

, THF, 4 d

1.

0

Halide, Sulfonate

PhCCH2Br

Brown,

2 . NaOH,

OH

*

II

H202

I

PhCHCH 2 B r 95%

* H.C. ; Pai, G.G. J Org Chem,

(86% ee R)

(19831,

48,

1784 Me

Li2NiBr4, 25"C,

THF

18h

*

Dawe, R.D.: Molinski, T.F.: Turner, J . V . Tetrahedron Lett, ( 1 9841, 1 . T i C 1 4 , LBuOOH " C 7 H 1 5CH=CHCH20Me

(r)

Klunder, J.M.:

CHzC12, 2 . Na2S04, RT,

96%

25, 2061 CI

-78°C +OM€! E t 2 0 nC7H15 HO

*

l h

Caron, M.; Uchiyama, M.; Sharpless, K.B. J Org Chem, (19851, 2,912

*

92%


NaI,

CH3CN,

SECTION 329

O°C

tBuOCl

*

I

'

Kometani, T. : Watt, D.S.*; Ji, T.; Fitz, T.

-J Org Chem,

50,

(19851,

5384

30 m i n

Gassman, P.G.*;

97%

quant

O'Reilly, N.J. Tetrahedron E,(1985),

26,

0

I

5243 OH

L i B H 4 , LBuOH,

II

THF

PhCCH2C1

1

*

PhCHCH2C1 76%

/CH2SSCH 2' C H NH C P h PhCNHCH "

*

I

COOH

(2,:)

1

HOOC

6

( 7 2 % ee S)

Soai, K. ; Yamanoi, T.: Hikima, H. J Organmt Chem, (1985),

-

0 \I

TBADH,

EtC(CH2)3C1

NADP, a q .

TRISSHC1 , H O C H 2 C H 2 S H 37°C

TBADH = T h e r m o a n a e r o b i u m b r o c k i i a l c o h o l dehydrogenase

*

iPrOH

Keinan, E. ; Seth, K.K.; Lamed, R. J Am Chem

-_--

290,

c023

OH

I

*

EtCH(CH2)3C1

82% ( 9 9 % ee S )

Soc, (19861,

108,3474

SECTION 329

-

ALCOHOL

0

CH212' THF,

33 1

HALIDE

Sm

*

0°C

n = l

* Imamoto, T. ; Takeyama, T.;

81 %

Koto, H.

Tetrahedron E ,( 1 9861,

n = O

3, 3243 82%

Tabuchi, T. ; Inanaga, J. *; Yamagkuchi, M. Tetrahedron Lett, (19861, 3, 3891 1 . Li2CuC14,

THF

\\to

4.75 h

>

CI

QOH

2 . HOH

Ciaccio, J.A.: Addess, K . J . : CI

Bell, T.W.

98%

*

Tetrahedron E ,( 1 9861,

3, 3697

(0:p = 6 0 : 1 8 % )

*

Umemoto, T. ; Kawada, K . ; Tomita, K.

-


3, 4465


SECTION 330: Alcohol, Thiol Bn - 0 Me&CHO H

Me,

,OTMS

H'

'Ph

c =c

TiC14,

SECTION 330

Ketone

-

0

HO +

Bn-0

Me (97

-78OC

Me

BnO

3)

:

no y i e l d * Reetz, M.T. ; Kesseler, K.; Schmidtberger, S.; Wenderoth, B.; Steinbach, R. Angw Chem Int Ed Engl, (19831, 22, 989 E ct, =c, Me

E t 11CN =CHCH n B u TMS

~

Et%{

BF3*0Et2, CH2Cl -78OC,

0

;

'CHO

H,

E

OH

t

y

y

30)

(70 86%

5 min Chem Lett, (1983), 1409

* Ando, W. ; Tsumaki, H.

--

1. nBuLi

2.

OH

I

CH3(CH2)3CHCH=CHMe

@=A r n b e r l y s t Cardillo, G.

3. I 2

-__)

@-NMe3+F-,

PhH

A26(F-) r e f 1ux

* : Orena, M.;

,f:MEM

1.

MeS

Braun, M.

19

co*

68%

Porzi, G.; Sandri, S.; Tomasini, C. J Org Chem, (19841, 2, 701 PhCHO

2 . HgC12

* : Hild, W.

CH3(CH2)3CHCEt

a q . MeCN

*

H OH

PhA/=2=2/ 57% (92% ee)

Angew Chem Int Ed w, (19841, 23: 723 ----

-

ALCOHOL

SECTION 330

KETONE

&"

0

I \

PhS02N-CH P h

*

KN(TFIS)2 -78°C

333

78%

*

Davis, F.A. ; Vishwakarma, L.C.: Billmers, J.M.; F i n n , J. J Org Chem, (19841, 49, 3241 -

*

-

1. nBuCH=CH2 PhH, 90°C

t

tB u C S N - 0-

Ax

*

t-BuO

2. Ni(R)

*

Curran, D.P. ; Scanga, S.A.; Fenk, C . J . -J Org Chem, (1984),

Osuka, A , * :

Taka-Oka, K.:

1.

0

I1

PhCCH3

Suzuki,

* H.

92%

3,3474

-.Chem

0;:"" ,

MeOH,

M o r i a r t y , R.M.:

HOU, K.-C.;

M o r i a r t y , R.M.;

HOU, K.-C.

Lett,

74%

(19841, 271

KOH

10°C

2 . 5% H 2 S 0 4 ,

H *-Bu (tto

CH2C12

*

19

P h C C H OH 54%

Prahash, I .

Org SE, (1985), 3, 138 Tetrahedron Lett, (19841,

-

25, 691


SECTION 330

0

0

I1

!C6H1

PhCHO,

3CCH2Br

O°C

+,

OH

I1

!C6H1

I

3CCH2CHPh

nBu3SnAl

Et2 81 % 30 m i n * Tsuboniwa, N.: Matsubara, S.; Morizawa, Y.: Oshima, K. ; Nozaki,

H.

-


EtCHO,

CrC12

t BuCCHCH

-t

I B r

THF,

RT,

* Dubois, J.-E. ; Axiotis, G.;

t-Bu

"< H

iP r C H O

,OB.o

/

c =c

81 %

Bertounesque, E.

*03

Ph

Me

26, 4371

\

CH3

2 . N(CH2CH20H)3

Hoffmann, R.W.

Me

24h


1.

25, 2569

>

Me

9) 85 %

* ; Ditrich, K.

Tetrahedron E ,(1984),

1. 2 IDA,

THF

2. S n C 1 2

-

' I

3. EPrCHO,

25, 1781

O°C

4. H ~ O +

M

.

HO P 60%

(58% ee)

Narasaka, K.; Miwa, T.; Hayashi, H.; Ohta, M. Chem Lett, (1984), 1399

--

0

r

SECTION 330

ALCOHOL

1. nBuLi,

2.

0

P h 3 C II CEt

3.

THF,

PhCHO,

-

-75°C

(99

1)

0

OH

0

0°C

*

Ph,C W

HOH

335

KETONE

P Me

h

Ph,C+Ph

t

99%

OH Me

1 . A1Me3 2.

PhCHO,

3 . HOH

Ertas, M.:

Seebach, D .

40°C

*

(5

PhCCH2CH3

nC H C H O , C H 2 C 1 2 - 3 7 PhBC12, i P r N E t 2 -78°C

*

Hamana, H. ; Sasakura, K.;

0 HO Ph%.Pr

Me (99

1 . NaN(TMS)2,

II

PhCCH2CH3 2. &N SO&

Davis, F . A . * ; Haque, M.S.

0 HO P h h . P r Me 1) 52%

SugaSawa, T. Chem Lett, (1984), 1729

-_c

0

99%

Helv Chim Acta, (19851, @, 961

0

II

95)

THF,

+

-78°C

0

Ph

77%

( 6 8 .5% ee S )

0 -J Org Chem, (19861, 51, 4083

PhIO, BF3 E t 2 0 , HOH OMe

Moriarty, B.M.*,’ Prakash, 0 . ; Duncan, M.P. Synthesis, (19851, 943

6 5%


H,

OH

0 II

1 . PhI(OCCF3)2, CHC13,

8OoC

10h

*

2. S i 0 2

* Tamura, Y. ; Yakura, T.;

0; CS iMe3

SECTION 330

77%

Haruta, J.; Kita, Y. Tetrahedron E,(19851, 26, 3837

nPrCHO, CsF, RT DMI,

3 min

'Q

OH

*

nPrCHC

-

II

0

55%

DMI = 1 ,3-dimethyl imidazol idin-2-one

*

Ricci, A.; Degl'Innocenti, A . ; Chimichi, S.; Fiorenza, M.; Rossini, G.; B e s t m n , H.J. --J Org Chem, (19851, 50, 130

' I +

6OoC,

,

* I d 64%

*

Matsumoto, T.; Ohishi, M.; Inoue, S. J Org Chem, (19851, 50, 603 1 . M e 2 C u L i , THF, 2.

O O C ,

3.

H,Ot

-78OC

15 min

3

* Koreeda, M. ; Luengo, J.I.

quant.

---J Am Chen Soc,

(19851, 107, 5572

SECTION 330

ALCOHOL

0

I1

EtCHO,

CH 2 = C H C C H

-

4OoC,

40h

1 % HRh( PPh3)4

*

acetone

(C-Tyr-OEt)2,

NO2

40°C,

w

CH C C C H E t 311 78%

Chem Lett, (19851, 1875

%to, S.; Matsuda, I. ; Izumi, Y.

Zn(N03)2,

337

KETONE

"$

*

HOH

\

NO2

24h

*

Watanabe, K. ; Yamada, Y.: Goto, K. Bull Chem Soc Jpn, (19851, ----

58,

Hob

1 . LDA

2 . TMS-C1

3. TPPO, C H 2 C 1 2 , - 7 8 ° C

4.

83%

PPh3

1401

69%

TPPO = t r i p h e n y l p h o s p h i t e o z o n i d e

*

Iwata, C. ; Takemoto, Y.; Nakamura, A . ; Imanishi, T.

C H =C

2 \

/SiMe20i

Tetrahedron Lett, (i985),

Pr

1 . mcpba, O O C ,

?'gH1 3

*

Tamao, K. ; Maeda, K.

2.

3227 0

CH2C12

5h

26,

+

II nC6H1 3CCH20H

3 0 % H 2 0 2 , KHF2 K H C 0 3 , MeOH RT,

3h

Tetrahedron Lett, ( 1 986) , 3, 65

72%


&

"'0

M e 0 OMe

e , KI KO;,

O

*

MeOH

M e 0 OMe

H

18)

(82

77%

* Shono, T. : Matsumura, Y.;

Inoue, K.; Iwasaki, F.

JCS Perkin ---

I , (19861, 73

0

ti

II

HO

CH 2 = C C C H 3 nC5H1, CHO

DABCO,

SECTION 330

THF,

72h

nC5H1 CHCCCH3 I1

t

CH 2

*

Basavaiah, D. ; Gowriswari, V.V.L.

65%

-


OH

K2Fe04, A1203, PhH

I

PhCHCH2CH20H

Kim,

3, 2031

C u S 0 4 . 5 H 2 0 , R T , 4h

* K.S. ; Song, Y.H.;

Q

*

P h C C H 2 C H 20H 95%

Lee, N.H.; Hahn, C.S.

-

Tetrahedron L e t t , (1 9861, 0 c1 II I 1 . PhS-CHFC6Hl3

3, 2875

2 . PhS-/tBuOK 3. 2.2 mcpba 4. HO-

*

Satoh, T.: Motohashi, S.; Yamakawa, K.

*

-

' c 6 H 1 8 0 H 83%

Tetrahedron L e t t , (1 9861,

3, 2889

SECTION 330

ALCOHOL

0

-

KETONE

339

OH

0

Sm/CH212

II

t

C H ~ C\ C /H - C H ~ C ~ H ~

I

II

C H ~ C C H ~ C H ~ C ~ H ~ ,

THF/MeOH , - 9 0 ° C

'0'

Molander, G.A.

* ; Hahn, G.

p

81 %

J Org Chem, (19861,

-78"C,

Maruoka, K . ; Hasegawa,

2596

& V

TiCl 4 , C H 2 C 1

~ ~ 'OSiMe, ''ph

51,

Ph

30 m i n

81 %

* M.: Yamamoto, H. ---J Am Chem Soc, (1986), 108,3827

1 . E t C H O , LBuMgBr

/

Tol'

T H F / E t 2 0 , -78°C

II 0

,,d1'\ 9

CH2CCH3 2 . A l / H g ,

THF,

*

Et 67%

0°C

a.

(64% ee)

Schneider, F.

* ; Simon,

0

R.


4% P d ( P P h 3 ) 4 ,

PhCH3

/ \ PhCH-CHCH20H

t

P h C H 2 C C H 20H

s e a l e d t u b e , 140°C

62%

60h

Vankar, Y.D.

* ; Chaudhuri,

N.C.;

Singh, S.P.

S 2 Coamun, (1986),

16, 1621


340

--

-

SECTION 331: Alcohol, "hi01 Bn-0 MeiikcHO H

SECTION 332

Nitrile

1 . TiC14, C H 2 C 1 2 - 78 " C

Bn 0

BnO

Me

*

(80

H OH 20)

2 . TMS-CN, -78°C l h 98% * Reetz, M.T. ; Kesseler, K.: Jung, A. Angeu --C h a t Int Ed Engl, ( 1 985), 2, 989 1 . B r C H 2 C N , g l y m e , Ni 85"C, 4 0 m i n

PhCHO

2 . aq. HC1

*

Ni

*

OH

I

t

PhCHCH2CN

84%

= N i I / L i / n a p h t h a 1 e n e / g l yme/RT/12h

Inaba, S.: Rieke, R.D.

Review:

.-v1

k

Albright, J.D.

'

*

-

*

-


26,

155

Equivalents from Cyanohydrins, Cyanohydrins and a-Dialkylaminonitriles"

i

~


3,3207

SECTION 332: Alcohol, Thiol

-

Olefin -- -

Allylic and benzylic hydroxylation (C=C-CH + C=C-C-OH, etc. is listed in Section 41 (Alcohols and Phenols from Hydrides).

QQ

SiMe,

dSiMe3 1. nBuLi, -85°C -I

Lo

8h 2 . O"C, H C 1

*

no y i e l d ( t h r e $ : e r y t h r o = 91 : 9 )

Mikami, K.; Kimura, Y.; Kishi, N.; Nakai, T.

--J Org Chem,

(1983),

48,

279

SECTION 332

ALCOHOL

CH3CH=CHCH2SiMe3

(L)

iPrCHO TiCl

-*CH2C1

- OLEFIN

341

+ , + + Me

-78"C, lh

( 97 92%

*

3)

*

Hayashi, T. ; Kabeta, K. : Hamachi, I : Kumada, M. Tetrahedron'Lett, - (19831, 2, 2865 0

LiA1H4 ~

~~

CH2CH20H H-C r N H M e

7

95%

( 1 00%

ee

CH N H P h * Sato, T. ; Gotoh, Y.; Wakabayaihi, Y.: Fujisawa, T. Tetrahedron Lett, (19831, 2, 41 23 0 0 It II HC(CH2)4CnBu

,

2 CH2=CIMe 4 CrC12

S )

C H 2 = C CI H ( C H 2 ) 4 C n B ~ OH

DMF, 25"C, 1 5 min

94%

Takai, K.*; Kimura, K. ; Kuroda, T. ; Hiyama, T.*; Nozaki, H. Tetrahedron Lett, (1983), 2, 5281

M e 2C = C = C H B r

P hCH *OL i , LB u OL i

*

OH

I

PhCHCH =C=CMe2

TH F / hexan e , r e f 1 ux 2h 65% * Harada, T.; Nozaki, Y.: Oku, A. Tetrahedron Lett, (19831, 2, 5665

342 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6 Li

SECTION 332

1.

2 . PhCHO

Wuts, P.G.M.

* : Thompson,

( t h r e o : e r y t h r o = 1OO:l)

P.A.; Callen, G.R. (19831,

-J Or6 Chm,

-

JX , Mn,

48,

5398

THF

c a t . 12, reflux overnight R = LBu X = Br ( a x : e q = 57:43) Hiyama, T.*; Sawahata, M.: Obayashi, M. Chem Lett, (1983), 1237 -R

R = H X = I

*

C a ( H g ) , T H F , 0°C 4h

>

R

89%

59%

Imamoto, T. ; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.: Mita, T.: Hatanaka, Y.; Yokoyama, M. --J Org Chem, (1984), 2, 3904

R = H

X = Br

P b , Bu4NBr, D M F ,

RT

86%

*

Tanaka, H.: Yamashita, S.; Hamatani, T.; Ikemoto, Y.: Torii, S. Chea Lett, (19861, 1611

--

T H F , -3OOC 1 .5h 2 . C H 2 ' C H C H O , -30°C-RT 3. aq. NH4C1, HC1 1 . Yb,

Phi

OH

*

I

Ph CHCH =CH2

66%

YoI$oo, K.: Yamanaka, Y ; Fukagawa, T.; Taniguchi, H.: Fujiwara, Y. Chem Lett, (1983), 1301

--

*

SECTION 332

ALCOHOL

-

OLEFIN

343

48%

DeRenzi, A.;

Panunzi, A.*:

Saporito, A . ; Vitagliano, A. 993

JCS Perkin 11, (19831, ---

1. nBuLi, -3O"C, CH30CH20CH2CH'CH2 2 . Et3A1,

--."A

THF

No>

l h -78°C

HO

3 . nBuCHO,

* Y . ; Yatagai,

*/

Yamamoto,

- 7 8 "C-RT

90%

H.; Saito, Y . ; Maruyama, K .

-J org

1. iBu3Al

Chm, (19841,

9, 1096

-$

, CH2C12, 25°C

2 . HC1 , 1 5 m i n

Mori, I . ; Takai, K . ; Oshima, K.: Nozaki, H. Tetrahedron, (19841,

82%

110,

4013 H

3.

a q . HC1

*

OH

(98% ee R)

Kawasaki, M.; Suzuki, Y.; Terashima, S. Chem Lett, (19841, 239 --


HOCH H O C H C S C C H OH

*

t

-

Et20/THF, RT

reflux

SECTION 332

2 , C =[: H'-

-

60%

Ishino, Y. ; Wakamoto, K.; Hirashima, T. Chem Lett, --

CH-OH

(19841, 765

S n , A l , RT t

aq. dioxane

c a t . AcOH, 24h

61 %

Nokami, J.*; Wakabayashi, S.; Okawara, R. Chem Lett, --

(1984), 869 OH

R'X

RCHO

S n , MeOH, e

R = P h , X = Br

I

RCHR '

t

-

AcOH, P t e l e c t r o d e ? 55"C, c y c l o h e x a n e

R ' = CH2CH=CH2

*

Uneyama, K.; Matsuda, H.; Torii, S.

91 %

Tetrahedron Lett, ( 1 984) , 3,601 7

R = iPr R ' = CH2CH=CH2

X = Bt(Q)2

-

-7!"c 3 . NaOH,

86% (90% e e S)

H2T2

Jadhav, P.K.; Bhat, K.S.; Perumal, P.T.; Brown, H.C. R = 3C6Hl3 R = (r-CH2CH=CHPh) X = OAc

-J Org .-Chem,

(19861,

51, 432

Pd(. P P h 3 I 4 , Sm12 THF, O'C, 2.5h

Tabuchi, T.; Inanaga, J."; Yamaguchi, M.

-

*

t


63%

3, 1195

SECTION 332

ALCOHOL

R = CH2-Tol R ' = CH2CH=CH2

-

345

OLEFIN

QCHZN3

-18OC

A

*

Sn(OTf)*, CH2C12 X = AliBu (87% ee S ) Mukaiyama, $.; Minowa, N.; Oriyama, T.; Narasaka, K. Chem Lett, (19861, 97 R = Ph

--

R ' = CH2CH=CH2 X = OP(O)[OPhI2

SnF2-Et2A1C1

95%

>

Matsubara,,S.; Wakamatsu,. K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K. ; Nozaki, H. Sots, (19851, 58, 1196 -.Bull Chem R = Ph 1 . B i , DMF , R ' X R ' = CH2CH=CH2 94% 2. RCHO X = Br

-

-

*

Wada, M.; Akiba, K. R = Ph R'

= CH2CH=CH2

*

-

Tetrahedron Lett, (19851, BiCl,,

X = B r

*

Zn

26, 4211

.>

THF, RT

99%

Wada, M.; Ohki, H . ; Akiba, K. Tetrahedron Lett, (19861, R = PhCH2CH2 R ' = CH2CH=CH2 X = GePh3

%no,

-

BF3:OEt2, CH2C12 -78°C - RT

*

55%

H.; Miyazaki, Y.; Okawara, M.; Ueno, Y.

Synthesis, ( 19861, 776

(E)-PhCH=CHCH2C1 PhCHO

3,4771

SnC12-A1,

aq. THF

*

>

Ph Ph

(threo:erythro

Uneyama, K.; Nanbu, H.; Torii, S. Tetrahedron Let.t, (1986),

87%

= 98:2)

3, 2395


SECTION 332

1. CH~=CH~H,

0'

PhCHO

2.

Tsai, D . J . S . :

P hCHCH 2CH =CHTMS

91 7: ( -Z :_E

120°C

= 78:22)

Organometdllics, (1983),

Matteson, D.S.

2,

236

1 . 2 EBuLi HO 2 Ph

A

2.

TiC14

3.

PhCH2CH2CH0

OH

*

4 . Me S i C H 2 C H = C H 2 5 . TM?I Imwinkelried, R.: Seebach, D.

*

I

PhCH2CH2CHCH2CH =CH2 (80% ee R )

Angew Chem Int Ed Eslgl, ----

3.

(1985),

75%

2, 765

NH4C1 /NH40H/HOH

Taber, D.F.*; Dunn, B.S.; Mack, J.F.; Saleh, S.A. J Org Chem, (1985), 50, 1987 OH

I

C H 3 C H CH C E C H

TiC14, CH2C1 2,

Me3A1

+

-78°C

87%

PH

CH3CHCH2CH =CHCH3

80%

2h

Wing, J . C . ; Fgrguson, G.S.; Moore, D.W.; Thompson, D .W.

J O m Chem,

Schultz, F.W.;

(19851,

50,

2124

SECTION 332 SiMe,

-

ALCOHOL

0

/ \

OLEFIN

, TiC14

1 . CH2-CH2

CH2C1 2 , - 1 00'C-RT 2 . 0.1N K O H

C a m , S.A.: Weber, W.P.

*

347

*

@OH

86%

J Org Chem, ---

Me3SiOOSiMe3, VO(acac)2,

(1985),

50,

2782

25°C

CH2C12

5h

Matsubara, S.; Okazoe, T.; Oshima, K.;

85 %

* Takai, K. : Nozaki, H.

Bull Chem Soc *,(19851, 58, ---

A

1 . iPrCH,CHO

Bubnov, Y.N. * ; Etinger, M.Yu. Tetrahedron Lett, (1985),

JC'

1 . NaBH4, C e C 1 3 , MeCN -15"C, 5 m i n 2. aq. HC1

Me0

844

->

bO"

26,

94%

2797

Me0

*

8 5%

Lakshmy, K.V.: Mehta, P.G.; Sheth, J . P . : Trivedi, G.K. Org Prep -hw: Int, (1985), 3, 251


348

SECTION 332

1 . A1Me3, T i C 1 4 E t \ Me20, p e n t a n e EtCH=CHCH2CH20H

20°C, 2 . HOH

(L) Moret, E.; Schlosser, M.

0

HO

+.Ph

CH2CH20H

Me / c = c \ H

5 5% Tetrahedron E ,(1985) , 26, 4423

*

1 . PhI,

*

3h

I

"gP Ph

2% Pd(PPh3)2(0Ac)2

Pip,

10h,

6OoC, 4 % C u I

2 . HCOOH

*

7 0%

Arcadi , A. ; Cacchi , S.*;

Marinelli , F.


* p

MeCeCl THF/Et20, Me0

9, 5121 h

'

+

-78°C

OMe

98%

30 min

Imamoto, T.*: Sugiura, Y. 2 Organanet Chem, (19851, t(, 7

aB.o 1

EtCHo

1. EMeCH=CHFH c1 Pet ether 2 . N(CH2CH20H)3

Et+

OH -

VC' +

E

Me

285,

+

q

Me

65%

5%

C021

CI

(96% ee)

Hoffmann, R.W.*;

Dresely, S.

Angew Chem Int Ed Engl, (1986),

c

3,189

SECTION 332

-

ALCOHOL

349

OLEFIN

L i I

4 [ CyN=Bu/MeMgBr]

w O"C,

20h 85%

*

Masset, P.; M a M a , S.; Viala, J.; Falck, J.R. Tetrahedron Lett, ( 1 9861,

-

1 . 4 CH2=CHCH2Br,

-5OC

OH

(+)diethyl tartrate 5 PhCHO 2.

THF, NaH, NaH

I

w

Sh

3, 299

P hCHCH2CH =CH2

82%

3 . SnC12

( 6 2 % ee S )

Boldrini, G.P.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. JCS Chem Comn, (1986), 685

---

OTf

I

fiCl O H 2 1 C=CH2

PhCHO, cat.

CrC12,

NiC12,

DMF

25°C

w

H CCHPh c C 1 o 21 1 OH

87%

*

Takai, K. ; Tagashira, M.; Kuroda, T.: Oshima, K.; Utimoto, K.: Nozaki , H. J Am Chem Soc, (1986), 108,6048 ---CH 3

PPh3, THF,

iPrOH

I

n P r C H = C H C C H 20H -

I

N 02

*

5% P d ( P P h 3 ) 4 , NaBH4,

5h

0°C

n P r CH=CH YHCH 2 OH

97)

Me

86%

+

n P r C H2CH= C'

CH

'CH

(3)

Ono, N. ; Hamamoto, I.; Kamimura, A.; Kaji, A. --J Org Chem, (19861, 51, 3734

20H 3

SECTION 334


+

Ph3PCH2CH2CH20H C 1 PhCHO

K2C03, iPrOH, 1 2 h

t

P h C H =CHCH2CH20H

84%

Cheik-Rouhou, F . ; Le Bigot, Y.; El Gharbi, R.; Delmas, M.*; Gaset, A. Commnz, (19861, 16,1617

Review: '!Double Asymmetric Synthesis and a New Strategy f o r Stereochemical Control In Organic Synthesis" Masarnune, S.

* : Choy, W.:

Petersen, J.S.; Suta, L.R.

Angew Chem Int Ed Eh@, (19851, 24, 1

Also via: Acetylenes-Alcohols (Section 302) SECTION 333: Aldehyde

, -

-

Aldehyde

'

1 . P h P h , 0 2 , MeCN D C A , 1 0 ° C , 3 0 min 2 . Me2S

DCA

t

88%

9,lO-dicyanoanthracene

*

Schaap, A.P. ; Siddiqui, S . ; Prasad, C.; M.

Palomino, E.: Sandison,

Tetrahedron, ( 1 9851,

SECTION 334: Aldehyde

-

Amide


41,

2229

SECTION 336

SECTION

E

335: E d (

q

-

-

ESTER

Amine

-9 Bn

Bn

I

I

(-Z ) - E t C H z C H O T M S , T H F BF3.0Et2, -78OC,

* Lounasmaa, M.

Koskinen, A . ;

c

351

94%

JCS Chem Carm, (19831, 821

1 .(MeS)2CH2, L B u O C l tBuOH, 2OoC, 4h

*

24h

2 . NEt3, CH2C12

b

Claus, P.K. ; Jgger, E.: Setzer, A . Honatsh Chem, (19851,

OCHO 1 . Br2

2. N E t 3 , H O H

Y

Bn

72%

116,1017

* Bn quant.

Duhamel, P.*: Kotera, M.; Monteil, T. Bull Chem Soc Jpn, (1986), ----

-


-

Ester

1 . Ac20/Py Ph

s To,

*

3,2353

2. C u C l , A c O H

*

OAc Ph

55%

Ogura, K. ; Fujita, M.: Inaba, T.; Takahashi, K.; Iida, H. Tetrahedron Lett, (19831, 24, 503


1 . Fe(CO)$

-2

, THF

DcozEt co

0

*

2* 3 . AcOH

C02Et

SECTION 336

II

HCCH2CH2CH(C02Et)2 62%

Tamblyn, W.H.

* ; Waltermire, R.E.

-


* -J Org Chem, Coates, R.M.

Cummins, C.H.:

(19831,

1. n B u L i , T H F , -78°C

iNHLBU-

H CnB u

2 . E-MeCH=CHC02Me

3 . AcOH

24,

2803

118, 2070 CHO

*

I

CH3CHCH2C02Me 60%

*

Baldwin, J.E. ; Adlington, R.M.; Bottaro, J.C.; Jain, A.U.: Kolhe, J.N.; Perry, M.W.D.; Newington, I.M. JCS Chem Coma, ---

1 . l o 2 , FleCN, h v methylene blue, OMe

*

2 . 36°C

93%

(19841, 1095

- 2 O O C

C0,Me no y i e l d

Jefford, C.W. ; Boukouvalas, J.; Kohmoto, S. Tetrahedron, ( 1 9851, 2, 2081

SECTION 337

ALDEHYDE

1 . LDA,

Ph

- ETHER

353

THF

2 . Me3SiC1

I I

CH3CH2CHC02Me

CHO

3 .tBuN=CHCN,

MeCN

I

*

C H CH CC02Ple

21

c a t . TMSOTf ~ . * C U ( O A C ) ~9,5 % MeOH

Ph

: Sekiya, M.

Okano, K.; Morimoto, T.

85%

JCS Chem Comn, (19851, 119

---

1 . CH3C(OEt)3 CHO

CH3CH2COOH , 2 0 0 ° C MeCH=CHCH20H

+

2 . a q . HC1

3 . 03, - 7 8 ° C 4 . Me2S, 0°C

68%

*

Carman, L.; Kwart, L.D.; Hudlicky, T. *Comnun, (19861, 1.

Enders , D Knoch, F. -.SECTION

*

Me

2 . LDA, THF, TMEDA, 3 . E-MeCH=CHC02Me 4.

16,169

G O M e NH2

EtCHO

I

CH3CHCH2C02Et

0 , C H C1

0:C

OHCd'CO,Me Me

-78°C

. ; Papadopdulos,2K. ;2Aendenbach, B ,E .M. ; Appel , R Tetrahedron E,(1 986),

337: Aldehyde

-

58%

;

3, 3491


1 .E-cBuOCH=CHCO2Me H CmC 0 2Me

iBuOH

2. Dibal-H 3 . MnO

Vo Quang, Y.; Marais,%.;

*

nB uOCH =CH C H O

Vo Quang, L.: Le Goffic, F.

Tetrahedron E,(1 9 8 3 ,

61 %

2, 5209


(CO)5MnSiMe3, PhCH 2CH 2 C H 0

Brinkman, K.C.:

LBuOH

OTMS

(C0)5MnH, CD3CN, 50°C >

Gladysz, J.A.


SECTION 338

I I

PhCH2CHCH0

7d

*

78%

Organcme$allics, (19841,

- Halide, SulfOMte

3,

147

CI

TMS-C1 , CH2C1 MeCH=CHCHO

(L)

HOCH2CH20H -1 5 ° C - r e f l u x

-


G i l , G.*

cH ( cH

L

1 . BBr3, 2 . KOAc ) CIC H

Satoh, Y . ;

25, 3805

pH 5

*

3. 30% H202

Br 1 CH ( C H ) 4 C H C H 0

Tayano, T.; Koshino, H . ; Hara, S . : Suzuki, A . Synthesis, ( 1 9851, 406 t

1 0 % ~ = C H O Hc i

nBuCHO

88%

CC14,

c1 2

70°C

65%

-

c1

I

n P r CH C H 0 99%

SECTION 339

ALDEHYDE

-

355

KETONE

I

r

TMS-C1,

o*o U

41

KI,

MeCN

*

0

Ll

2 2 0 ~ ,90 m i n

sieve,

F2,

FCC13

65%

F I

>

PhCH=CHOS iMe3

P hCH C H 0

-78’C

72%

i

4

*

Purrington, S.T. ; Lazaridis, N.V.: Bumgardner, C.L. Tetrahedron Lett, (19861, 27, 2715

-


6’

- Ketone

Br 1 . PhSCHTMS,

ZnBr2

2 . mcpba

3. heat

4 . H30t

Ager,

* D.J.

45%


“‘cf ’

0

HO

I\

OH

PdC12

CH2=CHCCH3 CuCl,

*

DME,

>

O2

5OoC, 2 0 h

5 u“‘ 0

0

Me

*

8 6%

Hosokawa, T. ; Ohta, T.: Murahashi, S.I. JCS Chea .-Comn, (19831, 848 -

-

Me


Akgiin, E.; Pindur, U.

*


1. tBuN=C, n PrCH -

,cu Bu

-

-78°C

=CHCHO

SECTION 341

, BF3*0Et2

0

II

0°C

-

2 . H30+

-

*

nBuCCHCH2CH0 I n Pr 90%

Ito, Y.; Imai, H.: Matsuura, T.; SaeguSa, T. Tetrahedron Lett, (1984), 25, 3091 1 . P0Cl3,

n

D M F , 45OC lh

2 . HOCH2CH20Na, 2h

*

Huet, F.

RT

-

*

45OC

DHO 3 6%



-

Nitrile

No Additional Examples SETION 341 : Aldehyde

-

Olefin

For the oxidation of allylic alcohols to olefinic aldehydes see also Section 48 (Aldehydes from Alcohols).

ALDEHYDE - O L E F I N

SECTION 341

C H 2TMS

357

CH 0

PhIO

I

I

B F 3 * O Et 2

Ochiai, M.;

* E.

Fujita,

dioxane

T e t r a h e d r o n s , (19831,

TMSOOTMS

OH

I

CH,CH(CH,)~CH=CHCH,OH

RuCl 2 ( P P h 3 ) 3

63%

2, 777

OH 1 CH~CH(CH~)~CH=CHCHO

70% Kanernoto, S.; Oshima, K.*;

Matsubara, S.; Takai, K .

E ,(1983), 2, 2185

Tetrahedron

CH2=CHCH0, - 2 4 ° C

K - 1 0 c l a y / F e +3 CH2C1 Laszlo, P.*;

Lucchetti, J .

Tetrahedron

1. tBuOK, 2 . DMAP,

CH2=CHCH2NHMe

THF, THF,

-78°C

-

Me2S04,

-78OC -78°C

RT PhH,

5 . a q . HC1, Senaratne, K.P.A.

RT

Tetrahedron

9..

E ,(1984), 25, 2147

3 . c y c l o p e n t a n o n e , THF 4.

Gilbert, J.C.*;

60%

reflux

I

49%

E,( 1 9841, 25, 2303


MeSCH = C H C H 2 S 0 2 T o l

zcCgH17 ) 3 NMeCl K O H , D M F , - 1 5OC 2 ' 1 2 H 2 5 Br 2 . TiC14, CuC12

+ !Cl

SECTION 341

2H25CH=CHCH0

RT - 5OoC 3 . K CO D M E , RT Ogura, K . ; Iihama, T.; Taiahaiii, K . ; Iida, H. Tetrahednxl Lett, (1984),

59%

*

-

1 . Me2NCH2CN, DMF K2C03, 48h 2 . A g N 0 3 , THF

Br

25, 2671

w

E t 2 0 , HOH Stela, L.

*


PhCH=CHCH20H

92%

25, 3457

K 2 F e 0 4 , a q . NaOH

*

PhCH=CHCHO

B n N E t 3 C 1 , P h H , 25OC 1 .5h Kim, K.S.*; Chang, Y.K.; Bae, S.K.: Hahn, C.S. Synthesis, ( 1984) , 866 Et2A1SPh, DCE 25' C ,

15 min

*

95%

YHO

,?""

V'8 4 %

(E : I = 39:61)

Takai, K . ; Mori, I . ; Oshima, K.*; Nozaki, H. WiIl Chen~Soc (1984),

---el

57, 446

SECTION 341

ALDEHYDE

Ph3As-CH2CH0 B r K 2 C 0 3 ( t r a c e HOH)

O U 0 CHO

Et20/THF,

* Y. ; S h i ,

HO 0 ,.H ' 1 OH21 S n w Bu

E tOCH=C

\

Me

*

3h

x

0

0

W P C H O 91 %

L.; Yang, J .

-


( PhIO)n,

26,

6447

DCC

"C, O H 2 1 C H = C H ( C H 2 ) 3 C H 0

B F 3 * O E t 2 , RT

77%

12h

Ochiai, M.; Ukita, T.:

/C H 0

RT,

359

OLEFIN

-

+

x Huang,

-

1.

Nagao, Y . ; F u j i t a , E. JCS Chem Corn, (19851, 637

---

EtMgBr,

-

0°C

Et20

RT

2 . a q . NH4C1,

0°C

/

*

EtCH=C

\

CH 3 Me

88% * Spangler, C.W. ; Tan, R.P.K.; Gibson, R.S.; McCoy, R.K. Syn CamRln, (19851, 5, 371

03

Me0

Me0

1 . CH(OEt)3, BF3.0Et2,

2 . NaBH4,

CH2C12 iPr2NEt

MeOH

3 . 6N H C 1

DasGupta, R.; Ghatak, U.R.

WCH

Me0 \

76%

*

Tetrahedron=,

(19851,

26, 1581


SECTION 341

Me I

OTBS

O

H

C

Me

TESCH=NtBu L

V secBuLi

* Schlessinger, R.H. ; Poss, M.A.; awe

OHC,

0-TB S

r;nrdv 77%

Richardson, S . : Lin, P.


CH2=CHCH0, cat.

RT

Yb(fod)3

48h * Danishefsky, S. ; Bednarski, M.

26, 2391

YHO

MeC

*

60%

Tetrahedron Lett, (1985) , 26, 2507

1 . 5% P d ( P P h 3 ) 3 ,

Ph N

Y

2.5% CF3COOH,

PhH 50°C

2 . 0.5N H C 1 , RT

* Murahashi , S. ; Makabe, Y.

*

I

Me 78%

Tetrahedron

s, (1985), 26, 5563

* 50°C, 4 h

Ph I CH2=CHCH2CCH0

88%

\I

/\

(E : Z- = 7 : 3 )

*

Suzuki, S.; Onishi, T.; Fujita, Y.: Misawa, H.; Otera, J. Bull Chem Soc *,(1986), 3,3287 --Also via: B-hydroxyaldehydes (Section 3210

AMIDE

SECTION 343

SECTION 342: Amide

n-NT 9 0

B

0 Et

-

-

361

AMINE

Amide -

1 . L D A , T H F , -78°C 2 . CH2=CHCH2CH2Br

*

T H F , -78 - 0°C 3 . O " C , 3N H C 1 4 . a q . Na2C03

87%

Fukuyama, T .*; Frank, R .K. ; Laird, A .A.

-

Tetrahedron Lett,

;

CH3CN=C

nBu

PhLi

/

\

*

TH F

CNHOFSe *

Lipshutz, B.H. ; Huff, B.; Vaccaro, W.

3501

II

CH3CNHCH2CCNHMe

A

Ph

87%


-

Also

0

It

nBu -

II O

0

via: Dicarboxylic acids (Section 312); Diamines (Section

SECTION .---

343: h i d e

-Amine

1 . secBuLi, TMEDA -78"C, THF

2 . TsN3 3 . NaBH4, Bu4NHS04

Reed, J.N.:

* Snieckus, V.

82%



t$kBr

PhNHMe,

0

KrauS, G.A.

* ; Yue,

12h

PhCHO,

DMF,

4 N2 0 Ph

*

j : u

---

1 % Z ~ ( O A C ) ~ 3,h

SECTION 344: Amide

-

>

Fle2C=C

76%

(1984), 2, 4889

Me

,OTMS

I

'OB n

B n N H CH 2 C C 0 2 M e ~7

CF3S03H,

; Achi.wa,

II

EtCNHCH2CH2NHi P r

Ester -

Bn

Bn

0

18 0 ° C

* 2 Org Chem, M.J. -

Ikeda, K.

50%

Sridharan, V.: Thianpatanagul, S. JCS Chem Cam, (19841, 182

iP r N H 2 ,

0 'N

Bn ' N U

90°C

O

Grigg, R. ; Aly, M.F.;

tN7

6 5%

Ph

H $ J COOH

Fazio,

7OoC

J Org Chem, (1983), 48, 2936 ---

S.

0

SECTION 344

K.:

CH2C12

1 . 5 h , RT Sekiya, M .

I

Me

83 %

-

Tetrahedron Lett

SECTION 344

-

AMIDE

363

ESTER

1 . e - , Et4NC104 0

P t electrodes MeOH

0

Okita, M.; Wakamatsu, T.; Ban, Y.

*

*

21

C02Me

4 nBii2CuLi

T H F , -10°C

cope

O %

55%

Heten>cycles, (19831,

NHBOC I BrCH C H C H

cO,Me

20,

401 NHBOC

*

I

* (95% ee)

nBuCH CH CH -

74%

21

C02Me

Bajgrowicz, J.Al; El Hallaouri, A . ; Jacquier, R.*; Pigiere, Ch.; Viallefont, Ph. Tetrahedron Lett, (19841, 25, 2231

0

tBuOH,

C C H C C 0 E.1 e II II 0 0

aoZ

hv

I

*

48h

'0 7 0%

Gramain, J.-C.*; Remuson, R.; Vallge, D. J Org Chem, (19851,

50,

710

0

II

3 BnOCNH2,

0

MeOH

II

CH2=CHCHNHCOBn

PhSeCH2CH=CHC02Me 6 i P r 2 N E t

I

3 NCS, 0°C

C02Me

*

Fitzner, J.N.: Pratt, D.V.: Hopkins, P.B. Tetrahedron Lett, (1985).

63%

26,

1959


OH

I

NHS02T01

SECTION 344

PdC12, C u C 1 2

I

CH2=CHCHCH 2CH

A c O N a , AcOH

I

Ph

CO,

*

R T , 2d

I

S02Tol 80%

Tamaru, Y.; Kobayashi, T.; Kawamura, S.; Ochiai, H.; Yoshida, Z. Tetrahedron Lett, (1 9851, 26, 4479 C02Me

C H =CHMgB r

1

C1 - C - N H C B Z

I

THF,

H

-78°C

*

* Castelhano, A.L. ; Horne, S.; Billedeau, R.:

C02Me

I

CH 2=CH -C-NH CB Z

I

H

65%

*

Krantz, A . Tetrahedron Lett, (1986),3, 2435

1 . L i N ( T M S ) 2 , THF -78°C 2.

(BnOC0)2, -78°C II 0

t

3 . AcOH, 0 ° C

Gore, M.D.; Vederas, J.C.

*

(R:S =

BnOCO II 0 2:98)

-

87%

J org Chm, (1986),51, 3700

Related Methods: Acid-hide (Section 31 5); Acid-Amine (Section 31 6 ) ; Amine-Ester (Section 351 )

AMIDE

SECTION 345

SECTION 345: Amide

( C O ) 5Cr=C,

/

-

ETHER

365

Ether, Epoxide, Thioether P h C H = N Me

OMe

H

t Me

Hegedus, L.S. Anderson, 0. P

hv,

* : McCuire,

.

0

Et20

M.A.: Schultze, L.M.;

J Am Chem ----

I

-

Soc, (19841, 106, 2680

PhSeBr,

CH2=CHCH2CH-C-OMe

II NnB u

MeCN,

* A. ; Terao,

0

O°C

12h

PhSe

Uemura, S. JCS Chem Comn, (1986), 530

K.;

80%

--PhSeBr,

20°C

AcNH(CH~)~CH=CH* MeCN,

*

12h

Toshimit s u , A. * ; Terao, K . ; Uemura, S. (1986), 1 . PhOCH2CC1 NEt3 2.

Me

7 5% Yijun, C.:

Ph

Ph

Toshimitsu,

-

CAN

'"as

66%

51, 1724 I=!

phoLJ1?H 0

70% * Antonini, I.: Cardellini, M . ; Claudi, F. : Moracci, F.M. Synthesis, ( 1 986 1 , 379


(TMS)2NCH0,

PhCHO

OTMS

CC14

5% CF3S03TMS,

SECTION 346

I

t

RT

PhCHNHCHO

lh

63%

* Johnson, A.P. ; Luke, R.W.A.; Steele, R.W. JCS Chera Corns, (19861, ---

1658

Halide, pulfonate -- --

SECTION 346: AmIde

8 CI

c12

0 II

~

~

~

~

(

~

FeCl ~________) 2 ~ ~ = ~ ~ d ig 1 yrne

20 )

2

I

reflux, lh

*

60%

Tseng, C.K. ; Teach, E.G.; Simons, R.W.

Syn C o m u n , (19841,

0 II

AcOH,

CH3 ( C H ) 6CNH

RT,

Na02Br

fi, 1027 CH3(CH2)6CNHBr

3h

81 %

*

Kajigaeshi, S. ; Nakagawa, T.; Fujisaki, S. Chem Lett, --

(1984), 2045 0

0 II

K

JHTs * -Xle

\

Ts,

2 1 2 , K2CO3

* Hirama, M. ; Iwashita, M.;

78%

I

Et20, RT, 1 . 5 h

(2:E =

Yamazuki, Y.;

2.7:l)

* Ito, S.

-


25, 4963

SECTION 346

AMIDE

L

HALIDE

L

3 . a q . Na2S03

68%

*

Knapp, S. ; Rodriques, K.E.

Tetrahedron Lett, (1985), 7

NBS, DME-HC1

"'CNH-S

367

NEt,

1 . Me,SiOTf,

n

L

-

0 To 1

-5OoC,

*

l h

*

Zefirov,

25, 1063

Kolbasenko, S . I . ; Kutateladze, A.G.:

-J Org Chem USSR,

CN-Cl,s o 2 * N.S. ; Zyk,

S02Tol 88%

95:5)

Tamaru, Y.; Kawamura, S . ; Tanaka, K . ; Yoshida, Z. Tetrahedron Lett, - (19841,

CH2C12,

26, 1803

I

(I,E =

Zyk, N . V . ; N i k u l i n , A.V.; Z e f i r o v , N.S.

I

(19841,

*

-6O'C-RT

20,

1209

0"' 0

'''~~0S02

90%

N.V.;

Kolbasenko, S.I.;Kutaleladze,

-J org Chm,

(19851,

53, 4539

A.G.


SECTION 347

1 . C0Cl2 2. C12

3 . HOH 4 . A1C13, C H 2 C I 2 ,

heat

5. HOH * Lambert, C.: Cai-llaux, B.; Viehe, H.G. Tetrahedron, (19851,

5 % a q . NaOH, CHC13

*a 70%

41,

3331

CI

SJ

c a t . Bu4NC1, 3 6 h Me Me ( 7 4 % c o n v e r s i o n ) 40% * Marcos, M . ; Castro, J.L.: Castedo, L.; Riguera, R . Tetrahedmn, ( 1 986), 9, 649 SECTION

3117:

Amide

-

Ketone

E t C H =C:

OTMS

nPr

-..& NHCO E t

0

1 . E t O CI1 N 3 ,

110°C

m

sealed tube

0

2 . Si02

56%

Lociuro, S.; Pellacani, L.*; Tardella, P.A. Tetrahedron Lett, ( 1 983),

-

OH

1 . NaH, T H F , 3 0 m i n 2 . C H 3L =i CO=hCCHFC3N

I

qj Blechert,

2, 593

c(+N"Ac

0

3 . HCOOH, H O H

* S.

Helv C h i m Acta, ---

65%

(19831, 68, 1835

SECTION 347

AMIDE

-

369

KETONE

ph%cHo

6 Mn(OAc)3 AcOH,

Nishino,

* H. ; Kurosawa,

1OO"C,

12 min 65%

Bull Chem Soc Jpn, (19831,

K.

01 , CH~CH=C< ,NMePh CH =C

2

THF,

\

CN

Ahlbrecht,

Me1

0

'3

CH 3

J

* H. ; Dietz,

7 6%


M.

1682

0

t

2 . H,OS

56,

0

I1 1 . E t O C C l , MeCN, ,OTMS 2 . CH2=C, nPr MeCN,

Akiba,

* K. ; Nakatani,

RT,

0°C

~

W

N

V

o

40 bEt

2h

84%

M.; Wada, M . ; Yamamoto, Y . --J Org Chem, (19851, 50, 63

1 . CH3CN,

Hg(N03)2 0°C

2 . NaBH4,

Stevens, R.V.

* ; Albizati,

HOH

O

W Me NHAc

81% K.F.

--J Org Chem,

(1985), .-50, 632


SECTION 348

0

1 . Ph3CNa, T H F

2. E N h P h , R T , 2 d

$Ph

3. H O H

*

Stamm, H. : Weiss, R. SECTION 348: Amide

-

0

65%

Synthesis, (19861, 392 Nitrile

CH2=CHCN, CH2C1 NaBH(OMe)3,

,,,, NHAc

-7OC

*

&CN

(I:E =

4:6)

Kozikowski, A.P.*; Scripko, J. Tetrahedron Lett, ( 1 9831,

1 . Hg(N03)2, CH2C12 AcNH2, reflux

nC H CH=CH2 - 4 9

2 . CH2=CHCN,

NaBH4, HOH

O°C

*

O&NH2 N H

1 . TMS-C1 , NEt3 ZnCl

2 . ZnC12, 80°C

3 . H30t * Rigo, B. ; Lespagnol, C.; Pauly, M. -J Heterocyclic

24, 2051

y 4H9

ACNHCH[CH~)~CN

Barluenga, J. ; Ferrera, L. ; Nijera, C. ; Yus, M. Synthesis, ( 1 984), 831 Y

7 0%

0

77%

H

91 %

e, (1 9861, 23, 183

AMIDE

SECTION 349

SECTION 349: Amide

-

371

OLEFIN

-Olefin

@

n

4 CF3COOH,

0d , & O H

0°C

t UATMS CH2C12, 2 h

0

*

90%

Hiemstra, H. : Speckamp, W.N.

4


*

FVP

,C02Me N-O C 0 M e

( 500°C )

Chu, M.; Wu, P.-L.; Civre, S.; Fowler, F.W.

Tetrahedron Lett,

I

C02Me

*

40%

Tetrahedtqn Lett, (1 9861,

Koch, K.; Lin, J.-M.; Fowler, F.W.'

Y

( 6FV 5 OPO C )

Cheng, Y.-S.;

-

f

OAC

*

Lupo Jr., A.T.; Fowler, F.W. J Am Chem Soc, (19831, ---OB n

""3

0;; ,

0

3, 461

(19831, 24, 1581

'(TPhAcO

24, 1407

b 0

74%

105, 7696

178°C

62h

Bremmer, M.L.; Weinreb, S.M.

*

Tetrahedron

93%

E ,(19831, 24, 261


,,,,\Se P h

0

0

"

SECTION 349

0

I1

N HCO, Bn

BnOCNH2, MeOH iPr2NEt,

-

~

0°C

HO""'

NCS

RT

80%

Shea, R.G.: Fitzner, J.N.; Fankhauser, J.E.: Hopkins, P.B. J Org Chem, (1984), 2, 3647 0

II

E t 2 A 1 C1,

RCCH=CH2

-

Q

- 1 3°C

R =

9R$3 %

(99.5% endo)

*

so;

(93% ee)

Oppolzer, W. ; Chapuis, C.: Bernardinelli, G. Chim Acta, (19841, -.Helv R

*

&3/

E t A l C1

*

-2OOC

67,1397

Rb 73%

R =

Oppolzer, W.

* : Dupuis, D.


6HMe 1 . secBuLi,

-78°C

2 . "C6Hl3I

*

-

TMEDA

26, 5437

OyNHMe

>

OeCgH

Beak, P. ; Kempf, D.J.: Wilson, K.D. J Am Chem Soc, (19851, ----

58%

m, 4745

SECTION 349

AMIDE

-

1 . TiC14, CH2C12 0 - 25OC

OLEFIN

>

2 . CH2=C=CMeSiMe2tBu

OEt

\

0 - 2 5 " C , 45 m i n 3. NEt3 4. H O H * Danheiser, R.L. ; Kwasigroch, C.A.; Tsai, Y.-M. J Am Chem Soc, (1985), ----

HNEt2, PhH 20 atm C O

0 II

nPrCH=CHCH20P(OEt)2

* Murahashi , S. ; Imada,

_______)

C3CCH2SiMe3

I

(CH212

II

nPrCH=CHCH2CNEt2

Chem Lett, ( 1 985), 1477

81 %

a. HCOOH

>

I

Ac

107, 7233

(El

Bu4NC1 , 50°C

Y.

67%

0

Rh6(C0), 6

(L)

N-YHnPr I OEt

373

wPr

2v-7 AC

68%

*

*

Hiemstra, H. ; Fortgens, H.P.: Stegenga, S.: Speckamp, W.N. Tetrahedron Lett, (1985), 26, 3151, 3155

Crimaldi,

* J. ; Cormons,

-

A.


60%

3, 5089


CH =C

2

iPr2NEt,

/CH2SePh

\

NCS

Ye

CH3

*

SECTION 350

s

CH 2 = C C H 2 N H C OtBu

I

Me

CH2=COhNH2 0

92%

Shea, R.G.: Fitzner, J.N.; Fankhauser, J.E.; Spaltenstep, A.: Carpino, P.A.; Peevey, R.M.; Tenge, B . J . ; Hopkins, P.B. J Org Chem, (19861, 52, 5243

Q tm-;;9

m-Pr

CH 2 C H = C H

I

3% P d 2 ( db a ) 3CHC1

> m-6~'

nPrCHNCC1

I8

nBu

m-BU

0 (83

18% PPh3

4

0

17)

69%

Henin, F.*; Muzart, J.: Pete, J . - P . Tetrahedron E,( 1 9861,

3, 6339

Review: IIAlkaloid Total Synthesis by Intramolecular Imino Diels Alder Cycloaddiltions"

Weinreb, S.M.

*

Accts Chem Res, ---

(1985),

18,16

Also via: Olefinic acids (Section 322)

- Amine ---

SECTION 350: Amine

1 . NH2CN, 2. HC1, nBuCH =CH2 -

NBS

EtOH

+

3 . Na2C03

4. a q . HC1,

J w g , S.-H.; Kohn, H q 7

2d

120°C

J Am Chem ---J Am Chem

Soc, Soc.

yH2 I

nBuCHCH2NH2

SECTION 350

AMINE

Q

1 . ( C ~ C O N O ) ~N ,O O"C, 4 0 m i n

"[

OMe

* R.C.

Et2?, b . MeLi,

2 . HOH

-

375

-78°C

58%

Organometallics, (1983), 2, 787

a. 3 LiNEt2,

-60

AMINE

t

2 . L i A 1 H 4 , THF

Becker, P.N.: Bergman,

CHO

-

NH,

VC14

-20

-

ooc]

2OoC, 1 7 h

&Me

*

Imwinkelried, R.; Seebach, D. Helv C h i m Acta, ( 1 984), --1 . T s - N = S = N - T s , P h H , RT 2 . P h M g B r , T H F , -60°C

3. P(OMel3,

MeOH

w

*

NHTS

-no *

THF, r e f l u x , 8 h Iahikura, M.; Kamada, M.;

3, 1496 NHTs

Natsugari, H.: Whittle, R.R.: Weinreb, S.M. ---J Am Chem Soc, (19841,

P d (QP P hC3 ) ql, ,K OB Hu 4 N B r

54%

* Terashima, M.

Synthesis, ( 1 984), 937

83%

106,7867

N

82%


9 KBar, H

RT,

2d

0 LN3

t

CH2C1 2/MeOH

SECTION 351

5 0%

* Matsumoto, K. ; Hashimoto, S.:

Ikemi, Y.: Otani, S. Heterocycles, (1984), 22, 1417

t

Y

PPh,Br-

1 . EDA, CHC13, 20°C 2 . 2 LBuOK, Et20 *

\1 PPh3Br-

t

3 . c C 3 H 7 C H 0 , RT 4 . H 2 / P d - C , MeOH

H

2!sH1 1

HNWNH 46%

*

Cristau, H.-J.*; Chiche, L. ; Plengt, F. SECTION 351: Amine n yr N-CH C 0 M e

*

I C g H 11


-Ester 1 . LDA, THF, -30°C 2 . Me1 t

CO, Me

wPr--J-

3 . H30 , 2 0 ° C

NH, 8 2 % (82% ee)

Bajgrowicz, J.AZ; Cossec, B.; Pigiere, C.L.; Jacquier, R.; Viallefont, Ph. Tetrahedron E,(1983), 24, 3721

C H 2 =NOBn

PhCH=C,

,OTMS

C02Me

OM e

10% M e 3 S i O T f ,

CH2C12,

7h

RT

*

I

PhCHCH2NHOBn

Ikeda, K.: Achiwa, K.; Sekiya, M. Tetrahedron Lett, (19831,

93%

2, 4707

SECTION 351

-

AMINE

1 . Et30

t

-

BF4 ,

0°C t

CH2Ci

L

8 min)

2. HOH(tln

\

377

ESTER

t E t 0 2 C ( C H 2 ) 3 N H 3B

F4-

61 %

* Smith, M.B. ; Shroff, H.N.

J Org Chem, (1984)) 49, 2900 Tetraedmn E ,( 1 9 8 3 ) 7 2 4 , 2091

OTlilS

Et02C

C O E t

H

B nN ( CH 2 S Me )

\OTMSOEt

CH2C12,

C02Et

?

30°C

Bn

5h

68%

*

Miyazawa, S . : Ikeda, K.; Achiwa, K.; Sekiya, M. Chem Lett, ( 1 984), 785. -B nN,

,C02Me I

c =c

/ SiMe3

Me02C

C02Me

CH20Me

Me3S iO T f

Me02C

CsF,

THF,

*

Hosorni, A. ; Sakata, Y.; Sakurai, H.

*

1 . 0.1N HC1, RT,

2.

Gull, R.; SchBllkopf, U.

*

Chem Lett, (1984), 1117 THF

NH; HCI

60h

8N HC1,

3. EtOH,

Bn

60°C

reflux

reflux

Synthesis, (19851, 1052

4 3 7:


SECTION 351

1 . LDA PhCH 2C02Me

2.

TMS-C1

3 . Py, PhN2+BF4-, 0°C 4. 5 a t m H2, Pd-C

Sakakura, T.; Tanaka, M.

*

DeShong, P. ; Kell, D.A.

C02Me

I

I C H CH CH

2 lN H B n

N I 02

EtCHC02Me

PhCHC02Me

73%

MeOH

*

JCS Chem Carm, (1985), 1309

: Sidler,

67%

D.R.

50, 2309

JOrg -.Chem, ( 1 9 8 9 ,

4 Et2CuLi, -6OoC,

Et20

3h

C02Me

1

*

E t C H C H CH

21

NHB n

7 0%

B a j g r o w i c z , J . A . ; El H a l l a o u r i , A . ;

V i a l l e f o n t , Ph.*

*

H; 2

J a c q u i e r , R.;

Tetrahedron, (19851, HC02-NH4 MeOH,

RT

t

,

10% Pd-C

P i g i e r e , Ch.;

5,1833

*

NH2

I

E t CH C 0 2 M e 67%

R a m , S.; Ehrenkaufer, R.E.

*


SECTION 351

AMINE

1 . CH =C NCH2C02Et

-

.Me

, THF

'CH~OA~

P d ( d p p e ) , 2OoC

tl

2 . 10% HC1, RT

HC

379

ESTER

*

NH2 I C H = C H C H 2 C H C 02Me

50%

CI

Ferroud, D.;

NCH2C02Me

li

PhCPh

Genet, J . P .

x

: Kiolle,

R.

-

T e t r a h e d r o n Lett, (19861, 3, 23

1 , L D A , THF, -78°C

2. CH2=CHCH20Ac

Pd(dba)2,

DIOP

t

CH2=CHCH2CHC02Me 7 5%

3 . 1 0 % HC1

( 3 9 % ee R )

4 . K2C03 DIOP =

(42,5S-)-(t)-4,5-bis-(diphenylphosphinornethyl) 2,2-dimethyl-1,3-dioxolane

Genet, J.P.":

'NH-

Bn

Ferroud, D.; Juge, S.:

Montes, J . R .

T e t r a h e d r o n -.Lett, ( 1 9861,

3,4573

\

C O , MeOH, R T , 8h

Lathbury, D . ; Vernon, P . ; Gallagher, T .

N/I

~n

*

'

CO,Me

67%

Tetrahedron L e t t , (1 986), 2, 6009

Related Methods: A c i d - h i d e (Section 31 5 ) ; A c i d - h i n e (Section 316); h i d e - E s t e r (Section 344)


SECTION 352: Amine

-

SECTION 352


Br

c)JH , MeCN

I

CH2C=CH2

I

P d ( O A c ) 2 , 100°C

O C H 2 C H =CHCH3

*

O X N S 60%

Shi, L.; Narula, C.K.;

Me.

k

Mak, K.T.: Kao, L.: Xu, Y . ; Heck, R.F. J Org Chem, (19831, 48, 3894 ---

Me3SiC1,

PhH

iPr2NEt,

80°C

L O T M S Me

*

ih

6h

I t o , Y.*; Sawamura, M . ;

2o

96%

Kominami, K.: Saegusa, T. Tetrahedron E ,(19851,

0 2N e PhH,

N

HS Ph

RT,

1 5 min t

B F3 .OE t

26,

5303

CJ,sNp&02H

8 5% Benati, L . ; Montevecchi, P.C.; Spagnolo, P. Tetrahedron, (1986), 42, 1145

OCH20Bn

1. PhLi, -10

I

gC5H, CHCH=NNMe2

2. HOH

-

Et20 25°C

OCH20Bn

* "C5H1

I

CHCHNHNMe2

I

Ph

Claremon, D.A.

* ; Lumma,

*

( t h r e o : e r y t h r o = 98:2) 95% P.K.; P h i l l i p s , B.T. J Am Chem Soc, (1986), 8265 --.--

108,

SECTION 354

AMINE

SECTION 353: Amine

381

KETONE

-Halide, Sulfonate

iPrCHiN3 C1 ( C H 2 ) 4 M g B r

-

Et20,

iP r C H ( C

C1-

15°C-RT

57%

2h

Courtois, G . ; Miginiac, P..

i P r N C1 CH 3 C - C - C02 Me

I

LI

(19831, I1148

NiPr

NaOMe/MeOH

11 I

- 7

wrll Chem Soc Fr, ----

reflux,

II

w

1 .7h

CH~CCHCI

*

De K i m p e , N. ; Verhe, R . ; De Buyck, L.; Schamp, N. Tetrahedron Lett, ( 1 985),

83%

26, 2709

Review: "Reactions of B-HaloenarninesT1

*

De Kimpe, N. : Schamp, N. SECTION 354: Amine

Org Prep Proc Int, , -

-,

(19831, 9, 71

-Ketone

1 . TsN=S=O,

PhCH3,

2.

RT

5% NaOH,

3 . 5 % H C 1 , 0°C 4. 0sO4, N a I 0 4

O°C

w Me

71%

*

G a r i g i p a t i , R.S. ; Morton, J.A.;Weinreb, S.M. Tetrahedron Lett, ( 1 9831, 24, 987

-


FV P

t

(6OOOC) 1o

- ~t o r r

SECTION 354

t

*

60%

Gordon, H.J.; Martin, J . C . ; McNab, H. JCS Chan Carm, (19831, 957

---

0 II 1 . Me2C=CCCH3, E t 2 0 RT OE t

King, F.D.

2 . 2N H C 1

*

2,3281

Tetrahedron Lett, (19831, 1 .AlCl,

60%

&

, DCE

H

I

S02Ph

1 1 . BF3'0Et2,

2 . OH-,

* Kakushima, M . ; Hamel,

Q t

Y H 2 ?Me

DCE:,

dioxane

92%

Q-t H

64% P . ; Frenette, R.; Rokach, J. -J Org Chem, (1983) , 48, 321 4

n C 6 H 1 3CH0

>

d 0

n C 6 H 13

PhH, r e f l u x CH2-CCH=CH2 95% OMe Overman, L.E. ; Kakimoto, M . ; Okamki, M.E.; Meier, C.P. J Am Chem Soc, (19831, 105, 6622 ----

SECTION 354

-

AMINE

383

KETONE

NMe2, L i C 1 0 4

e

,

rotating disk

electrodes

Renaud, R.N.

Q

Matsumoto,

0 Me

* ; B&&,

,

MeCN

D.; Stephens, C . J . Can J (19831,

e,

CH2(NMe2)2,

MeOH

"high pressure, RT,

58%

61,1379

&NMe2

KBar" 53%

24h

* K . : Hashimoto,

S.; Otani, S . : Amita, F.; Osugi, J.

Syn Camnun, (19841, fi, 585 --

0 I1 1 . BrCH2CCH=CHPh Et20,

2. NEt3,

24h

*

PPh3

CH2C12, 3. LiA1H4,

U

2h Et20

Me

A

P

78%

-

Ghi rlando Y R . ;

0

Howard, A.S.*; Katz, R.B .; Michael, J . P . Tetrahedron, ( 1984), 40, 2879 1 . L D A , THF,

*

-78OC

2 . Me3SiC1 3. MeLi,

h

THF/Et20

* Me0

4. MeOQFH-N3 OTiCl

J

73%

Seebach, D.*; Betschart, C.: Schiess, M. Helv Chim Acta, ( 1984) , 3, 1593

---


SECTION 354

( -exo:endo = 4 . 2 : l ) * Grieco, P . A . ; Larsen, S.D.; Fobare, W.F. Tetrahedron Lett, (19861, 3,1975 1. nBu3SnCH2NEt

0

0

It

Me2CHCC1

-

2 2OoC, 1 5 m i n

2 . 3N H C 1

*

0

II

Me2CHCCH2NEt2

3 . 3N NaOH

64%

Verlhac, J.-B. ; Quintard, J.-P.


h\C/NH P h

1 . P h M e C = N P h , A1C13 d i o x a n e , 100°C

I1

CH CI = N H

Ph’ Barluenga,

2. LiA1H4, 3 . H30t

* J. ; Cuervo,

Satoh, T.; Kaneko, Y . ;

THF

2,2361

PhCHNH P h

I

*

FH2

cI =o Ph

56%

H.; Olano, B . ; Fustero, S.; Gotor, V.


* K.

Sakata, K . ; Yamakawa, Bull Chem Soc Jpl, (19861,

----

97%

2,457

SECTION 355

AMINE

-

3 85

NITRILE

fl:: eH

Amine - Nitrile -.SECTION 355: -

17

P Ph SB Su P3 ,h T H F

N-OH

Barton, D.H.R.;

H,N

Simon, E.S.: Zard, S.Z. JCS -.Chem -.C a m , (19841, 337

-

Zn12

15 min

3CH0

tN

-6

Fife, W.K.

*

TMS-CN,

-7°C

Me2NiC1, C H 2 C 1

I

t

83%

25, 4583

>a+ 0 ' \

N

CN

NC

Heterocycles, (19&4), 22, 93, 1121 1 . TMS-CN

PhCH =CHCH=NPh

Prajapati, D.;

nC6H1 3 C H N H 2

( 96

0

2. l h b r u s h , R.C.;

*

CN

2 . N H 3 , MeOH 4 0 ° C . 2h * Mai, K . ; Patil, G. Tetrahedron Lett, (19841,

0

y i eI d '

CN

Motherwell, W.B.;

1 . TMS-CN, nC6H1

' good

2 . AcOH NaCN

AcO

*

Sandhu, J.S.

N

4)

95%

CN

I

PhCH =CHCHNHPh

* ; Baruah,

90% J.N.

Ind J Chem B y ( 1 984), 23, 853 ----


CN I P h C H O T M S , MeOH

Me

r e f l u x , 2h

Ph

*

Mai, K . ; P a t i l , G.

Me t

It

CH3CCH3

*

Mai, K . ; P a t i l , G.

=

Syn Carmu, (19841,

2 . RT, TMS-CN 3 . lOO"C, 1 min 4. R T Syn -Ufly

H Ph

(RR:RS

1 . BnNH2, neat lOO"C, 1 min

0

SECTION 355

CN Ph

97%

3:l)

e,1299 CN

I

>

CH3CNHBn

I

CH 3

97%

(1985)s 15, 157 Inti',( 1985) , 2,183

Org P r e p Pnx: -

1 . t B u M e 2 S i O T f , CH2C1 2 , 0°C 2. M e L i , T H F , 0°C 3. CH2C12, TiC14 - 7 8 " C , 30 m i n 4. T M S - C N , -78°C-RT 5. a q . NaOH

-0

Tokitoh, N . ;

O k a z a k i , R.

W N CN , M@

w

63%

Chem L e t t , (1985), 241

1 . P s S e S e P h , NaCN AcOH, 5 d , 2OoC

H Barton, D.H.R.

*

*

2. a q . NaOH ; B i l l i o n , A.; B o i v i n , J. T e t r a h e d r o n -.Lett, (1 985),

H

95%

26,

1229

AMINE - OLEFIN

SECTION 356

387

SECTION 356: Amine - Olel'in - -

CH2=CHBr, 100°C H

4

P ~ ( O A C ) ~ ,P ( g T o 1 )3 CH2=CHCH(OMe)2

OMe

C / , d O M e

~

57%

F i s c h e t t i , W.; Mtk, K.T. ; Stakem, F.G.; K i m , J.-I.; R h e i n g o l d , A.L.; Heck, R.F. -J Org Chem, (19831, 48, 948

Br

I

I

CH2=CCH2CH2CH2CH=CH2 H

Narula, C.K.:

Pd(OAc)2, P(oTo1 ) 3 1 0 0 ° C , 66h

Mak, K.T.:

CH2=C=CH(CH2)3NHPr

Heck,

71 %

* R.F.

--J Org Chem, (19831, 48,

2792

ASB Fq

P

dioxane ref1 ux

a-Pr

95%

Tetrahedron .-Lett, (19831, 2 2 , 3997

A r s e n i y a d i s , S . ; Gore, J.

o +Vp-s, gu 6;;; P d ( O A c )2

CH2=C=CHnBu

dPPe

______)

:::*r

Shimizu, I . ; T s u j i , J.

ux

-Chem L e t t ,

Ph ( 3

:

(19841, 233

I ) Ph

65%


*

SECTION 356

7 5%

z, (19841, 25, 4437

Tamura, R. ; Hayashi, K . ; Kai, Y . ; Oda, D.

Tetrahedron

0""'

1 . CuCN 2.

Ishikura, M . ; Kamada,

*

CH2=CHCH2Br

* M . ; Oda, I. ; Termhima, M. Heterocycles, ( 1 985), 3

6 9%

117

: Termhima, M. Heterocycles, ( 1 984 1 , 22, 2475

Ishikura, M.; Kamada, M.; Ohta, T.

CF3COOH, CH3CN,

Overman, L.E.

* ; Burk,

2h

82°C

H H

90%

R.M.

Tetrahedron

Lett, (19841, 25, 5739

C HCHO F3COOH Me3SiCH2CH=CHCH2CH2NHBn

-3 Y

Bn

a q . T H F , RT

Grieco, P.A.

* ; Fobare,

56h

W.F.


81 %

3, 5067

SECTION 356

-

AMIFlE

1. nBuLi,

hexane

reflux,

20h

2. I-PhCH=CHBr, PPh MeLi, 3 . a q . 3 i H C1

Murahashi , S.-I. ; Naota, A

389

OLEFIN

PdCl PhH,

* reflux

*

4.. ; Tanigawa, Y . -Org Syn, (19841, 62, 39 n

67%

Me2C=CH ) 2 C u L i t (OMe

Et20, r e f l u x

GO% Germon, C . ; Alexakis, A . ; Normant, J.F. B u l l Chem Soc Fr, (19841, I1377 -,--I. CH3CH=CHCH0

OH-HCI, KCN

HOH, 2.

*

EtMgBr,

0°C-RT THF,

0°C-RT

ANbrecht, H. ; Dollinger, H.

Synthesis, (19851, 743 t

[ R h - ( R - b in a p ) , ] C l

+NR2

120"C,

>

3h

78%

O4 - T p N E t 2

18h

(100% ee S )

binap

*

Tani, K . ; Yamagata, T.; Tatsuno, Y.: Yamagata, Y.: Tmita, K . ; Akutagawa, S.; Kmobayashi, H.: Otsuka, S. Chem Int Ed Engl, (1985), 24, 217 ---

-


PhNH2,

HgC12-K2C03

THF-HOH,

Barluenga,

* J. ; Aznar, 1. TiC14,

SECTION 356

7OoC I

Ph

F.; Liz, R . ; Cabal, M.-P. JCS -.Cheg Ccmn, (1985), 1375

-

-

5h

NH-B n

NH-B n

NB n - 7 8 O C SnBu3 RT, Keck, G.E.*:

78%

l h

-J Org

Enholm, E . J .

TMS

h e d - S c h o f i e l d , R.:

' Me

1)

(23

(19851,

C-,

* P.S.

CH2=CHCH 2SnMe3 ho, MeOH t

Berg, R.M.:

Mariano, P.S.

50,

15%

5667

Qy Me

*

146

TMS

60%

Mariano, -J Org C k a , (19851,

c104-

50,

-

\

71%


3, 2821

SECTION 356

-

AMINE

391

OLEFIN

1 . MeCH=CHCH2-B Et20,

PhCH =NPh

*

ye

-78°C

2 . HC1, 0°C 3 . a q . NaOH,

-

Phy=V,

>

NHPh

RT O°C

93%

YamamOto, Y. ; Komatsu, T.: Muruyama, K. J Org C-, (1985), CH2=CHCH20H,

50,

1 2 0 - 1 50°C

t

PhNH2

P t C l 2( P P h 3 ) 2 - S n C 1 2 - 2 H 2 0

CH2=CHCH2NHPh

Tsuji, Y.: Takeuchi, R . ; Ogawa, H.; Watanabe, Y.

-Chem L e t t ,

NPh

CH2=CHCH2SnBu3,

II

PhCCl

3115

PdC12(PPh3)2,

67%

*

(1986), 293

PhH

120°C

NPh

t

II

PhCCH =CHCH

8 6 7;

1 Oh

*

*

Kosugi, M. ; Koshiba, M.: Atoh, A . : Sano, H.; Migita, T. Bull C b -.Soc (1986), 2,677

s,

CH * 0 S 0 2 M e I

TKSCH2C =CH PhCH=NPh Ni[P(OEt)3]4,

PhCH3

reflux, overnight

Jones, M.D.;

Kemitt, R.D.W.

*

b\

Ph

Ph

77%

JCS C k m colea, (1986), 1201


T r o s t , B.M.

* ; Chen,

S.-F.

SECTION 357

s,

J Am Chem Soc, (19861, . 6053 SPh

C H 2CH *N3

CHC13,

I

CH =CCH =CH2 I

SPh

Pearson, W.H. Glens, J . H .

* ; Celebuski,

70°C 3d

L W

62%

Poon, Y.-F.;

J.E.;

/-A

*

Dixon, B.R.;

-

Tetrahedron Lett, (1 9861,

Reviews:

2,6301

"Diels Alder Reactions of Azadienes" Boger, D.L.

*

Tetrqhedron, (19831, 39, 2869

ttSynthesis of Primary A l l y l i c Aminesll Cheikh, R.B.;

Choabouni, R . ; Lament, A , ; Mison, P . ; N a f t i , A . Synthesis, ( 1 983 1 , 685

"Recent Advances i n t h e Chemistry of Conjugated Enmines" Hickmott, P.W.

*


SECTION 357: Ester

C.W.

*;

2989

-Ester 1 . Pb(OAc)4,

Rubottom, ( Y O S i M eG.M. 3

40,

CH2C12

R T , 3 0 rnin 2 . E t 3 N H F , RT Gruber, 3.M.; Marrero, R.:

J Org ---

Juve J r . , H.D.;

Chem, (19831, 48, 4940

66% Kim,

SECTION 357

ESTER

0

P h CCH 2 C H 2 C O O H

HC(OMe)3, H O H

* ; Peterson,

82%

4h

7 9%

2,1469


J.R.

E n 3 ( OAc ) 7 AcOH,

40°C

24h

* ; Kang,

64%

M.

---J Am Chem

Soc, (19841,

1 . LDA, - 7 8 ° C THF/HMPA

2 . MeCH=CHC02Et -78OC

Yamaguchi, M.*:

PhCHCH *C02Me

-

'OH

nPrC02Et -

I

t

R.A. ; Katz, A.H.; McKillop, A.H. -J Org Chem, (19841, 9, 3840

4 0'

Corey, E.J.

C02Me

2.8h

* : Conley,

Fristad, W.E.

3 93

ESTER

T1 ( N 0 3 ) 3 * 3 H 2 0

II

Taylor, E.C.

-

3 . a q . NH4C1

Me

+

Et+,

CO,Et C0,Et

(20

106,5384 ye E t p , 'OFt

C02Et

1)

a7 % Tsukamoto, M.; Tanaka, S.: Hirao, I. Tetrahedron E ,( 1 9841, 25, 5661


"

Bn

,>\+--(

0 . 1 PdC12,

OH

Hood t

CO,

AcOH,

NaOAc,

I d

bo

3 CuC12 RT

SECTION 357

*

0-

0 : Me

84%

*

Tmaru , Y.; Higashimura, H.; Naka, K.; Hojo, M.; Yoshida, Z. Angew Chem Int Ed 9,( 1 985), 2,1045 ---I-

0

Mn30(0Ac)7,

AcOH t

3 . 5 H02CCH2C02Et 23OC

* Corey, E.J. ; Gross, A.W.

7 5%

-


26,

4291

THF - 1 00°C

CO, Me

Z-MeCH =CHC02Me

54%

(erythro:threo = 75:25)

* Corey, E.J. ; Peterson, R.T.

-

Tetrahedron Lett, (1 9851,

Me0 C C H C 0 Me

PhCH3, MeOH,

26,

CO,Me

CAN

RT

5025

*

&,Me

5 9%

(2:m:p = 5 1 : 2 1 : 2 8 ) Baciocchi, E.*; Dell'aira, D.; Ruzziconi, R.

-


ESTER

SECTION 358

0

ETHER

1 . S m 1 2 , T H F , O°C

0

II

-

II

HC(CH2)40CCHCH3 I Br

395

0

2. A c 2 0 , D M A P

82%

Tabuchi, T.; Kawamura, K.;

Inanaga, J.*: Yamaguchi, M. Tetrahedron Lett, ( 1 986), 3, 3889

Also via: Dicarboxylic acids (Section 31 2 ) ; Hydroxyesters (Section 327; Diols (Section 323) SECTION

358:

Ester

- Ether,

Epoxide, Thioether

CH CH COOH

l 2

cat. HgO

C

111 * L

\

( C H 2 )30H

DMF,

*

reflux

73%

2h

Yamamoto, M. ; Yoshitake, M.: Yamada, K . JCS -.Chem C a m , (19831, 991

-

-

5 CH2=C(OMe)2 PhCH3, llO°C 15h Boger, D.L.

i

; Mullican,

M.D.


86%

2, 4939


SECTION 358

:H2CO2Et C02Et

*

o*o

Ac20,

K

A.D.

oA

AcO

c a t , H2S04

RT, 1 0 h

* W.F. : Rivera,

83%

--Bull Chem Soc a, (19831, 5, 1428

: Takeuchi , R.

Watanabe, Y . ; T s u j i , Y .

Ph

u

oAo

12OoC, 6h

C02Et

Bailey,

CHC02Et

*

OAc

*)i

96%

J Org Chem, (19841,

9, 4958

H 2 N B S , CC14 22"C,

*

2h

C H 2 C H 2 C H 20H

Williams, D.R.

/ OTMS

65%

* ; Harigaya, Y . ; Moore, J.L.; D'sa, A. J Am Chem SOC, (1984), 106,2641 ---0 II

PhCCH3,

50°C

MeCH =C. \

(L) O E t

Yamamoto,

1 0 KBar,

* Y . ; Maruyama, K . ;

OTMS

*

I

PhCHCHC02Et

6d

I

Me

85%

( e r y t h r o : t h r e o = 55:45)

Matsumoto, K . Tetrahedron Lett ( 1 984),

-

25, 1075

SECTION 358

ESTER

Me

-

397

ETHER

-

I>- k - 0 S i M e 2 t B u I

PhCH=CHC02Me

/ 0\

OOCPh

II

0

Pd(OAc)2,

CH2C12,

Nagata, R . ; Matsuura, T.; Saito,

PhCH -CHC02Me

8h

* I.

59%

Tetrahedron Lett, ( 1984) ,

1. COY CBuLi,

25, 2691

-110°C

TH F / p e n t a n e / E t 2 O 2.

C O Y 2h,

-110'C-RT

3 . Me1

5 5%

*

Seyferth, D. ; Hui, R.C.

Organmetallics, (1984),

t

1 . Fle2S-SMe B F 4 MeCN,

2.

RT,

O'Malley, G . J . ;

*&

-

30 min

iPr2NEt,

MeCN

'5

36h

Cava, M.P.

x, 'CHO


*

5% Zn12,

Kita, Y . ; Yasuda, H.; Y.

S Me

86%

*

.OS it 4 e 2 t B u C H =C 'OMe

0

2, 327

MeCN,

-

48h

c

C

0

2

M6 7 e%

OSiMeetBu RT ( a n t i : s y n = 96:4) Tamura, 0 . ; Itoh, F . ; Ke, Y.Y.; Tamura,

O0C

-

Tetrahedron

E ,(


SECTION 358

OTMS

I 1C5H1

CH2C12, 20°C

CHCHO

t

2 . Py

B n w C O z E “‘gH1 1

*

*

Oshino, H.; Nakamura, E. ; Kuwajima, I. -J Org C h e ~ , ( 1 985), 0 II E t O Z C C H 2 S M e , CH2C1 SnC14,

Stamos, I . K .

*

Murota,

0°C

-

RT

* K . ; Matsuda,

A.:

50, 2802

&&


CO/HOH, 5h

93%

MeSCHCOZEt

95%

26, 477

C O ~ ( C O ) ~ y, - p i c 0 1 i n e

MeOCHzOMe

OSiMe3

MeOH, 1 6 0 ° C

t

MeOCH2C02Me

(65% conversion)

Masuda, T.

--will Cheto S o c a ,

(19851,

50%

58,

2141

l

~

PdClZ, CuC12 A c O N a , AcOH OH

OH

Tamaru, Y.;,Kobayashi, Yoshida, Z.

CO,

RT,

t P

h

Id

80%

T.; Kawamura, S.; Ochiai, H.; Hojo, M.; Tetrahedron Lett; (1985),

26,

3207

~

o

ESTER - ETHER

SECTION 358

0 II PhCS-SePh,

399

0 II

AIEN

PhH, r e f l u x ,

“3 ePh

17h

54% E, 1 0 % I * Toru, T. ; Seko, T.; Maekawa, E. Tetrahedron Lett, ( 1 985), 26, 3263 0

\

STol

6

Marino, J . P .

*

STol

2 . Al(Hg),

a q . THF

; De l a Pradilla, R.F.

Tetrahedron E ,( 1 985),

68%

26, 5381 Me

______)

AcOH ,

Ferroz, H.M.C. Zocher, D.H.T.

* : Brocksm.

Pinto, A.C.:

Tetrahedron 0 II PhCCl

Abla, M.A.:

s, (19861,

3, 81 1

, NEt3/MeCN

OOC-RT,

Hormi, O.E.O.;

T.J.:

85%

N a m a n , J.H.

12h

*

Carmun, (1986),

61 %

16,69

400


S EXXION 359: Ester ---

C02Et

-Halide, Sulfonate C02Et

NaH, T H F , - 2 0 ° C

I

PhCHC02Et

Barnette, W.E.

*

SECTION 359

~ T o SlO 2 - NI

I

>

A

PhC-C02E t

I

F

F

J Am Chem Soc, (1984), ----

81 %

3,452

I

I

85% T q a r u , Y . ; Mizutani , M. ; Furukawa, Y ; Kawamwa, S. ; Yoshida, Z . ; Yanagi, K . ; Minobe, M. ---J Am Chem Soc, (19841, 3,1079

.

0

I1

E t 2 N S F 3 , 0°C

PhCCH2CH2COOH

Patrick, T.B.

CHC13, 3 0 m i n

* ; Poon,

* 85%

Tetrahedron=,

Y.F.

PhN2

+

C1

- ,

KI

C H =CHC02Me

*

(19841,

25, 1019

I

I

PhCH2CHC02Me

E t O H , 30"C, 3 0 m i n Ganushchak, N . I . ;

Obushak, N.D.;

Polishchuk, O.P.

---J Org Chem USSR,

(19841,

g,595

45%

-

ESTER

SECTION 360

1 . C12, CC14,

2 . Bu4NC1,

401

KETONE

MeCN

RT,

8h

3. a q . H202

Morella, A.M.;

*

Ward, A.D.

82%

Tetrahedron Lett, ( 1 985), KF,

26,

2899

CH2Br I

reflux

8h

Anzeveno, P.B.

CI

*;

Campbell, J . A . ; White, W.L. Syn Cornnun, (19861,

QCN

1 .MeCN,

2.

2-r

CN Robert, A.

*.

97%

NaOCl

16, 387

CI

pH 5 - 6 48% H B r

iPrOH,

reflux,

3h

Jaguelin, S. : Cuinamant , J . L . Tetrahedron, (19861,

0

2,2275

8 3%

Also via: haloacids (Section 31 9) ; Halohydrins (Section 329)

SECTION 360: Ester

CH2=C

/Me

\

Ketone e-,

1. EtNO2, cat,

C02Me 2 .

Monte, W.T.;

-

MeCN

PhN=NPh,

-

Bu4NBr

e , MeCN 0 2 ’ Bu4NBr

Baizer, M.M.;

*

L i t t l e , R.D. (19831,

-J Org Chem,

li

rH3 CH3CCH2cHCO2Me

60%

2, 803


c1

OTMS

I

1 . PhSLHCO2Me,

PhC=CH2

L e e , T.V.

1 . TiC14/CH2C12

Fleming,

* I. ; Iqbal,

6

Me0

0 ZnBr2

2. Ni/H2

* ; Okonkwo,

2.

92%

(19831, g,323 73%

Tetrahedron E ,(1983), 2,327

J.

1 . BrZnCH2C02Me

2 . CAN

Pearson, A.J.

* ; Richards, 1.

-nC5H, CCH3

It

PhCCH2CH2C02Me

Ni(R)

F e ( C 0 I 3 PF6-

-8

C02Me

9 0%

I.C.

Tetrahedron Lett, (19831, 2,2465

&CH20Me Y NH2 THF,

2.

LDA,

-78°C

3.

PhCH=CHC02Me

4 . 0 3 , CH2C12,

Enders, D.

p

Tetrahedron=,

J.O.

SECTION 360

t 59%

-78OC

C 0 2- M e

* : Papadopoulos,

K. Tetrahedron Lett, (1983), 24, 4967

86%

Mander, L.N.: Sethi, S.P.


ESTER

SECTION 360

KETONE

-

1 . base, CH2=CHCCH3

0

I '

II

*

403

THF, 20°C CH,C(CH,),CH(CH,),CO,Me 2 . M e O H / N a O M e , 0°C 3. AcOH 93% Huggenberg, W.;

Hesse, M.

* --Helv Chim Acta,

0II 0II 2C8H1 7C-C-COR

*

Rh2(0Ac)4,

L

R* = Taber, D.F.

&I K.

MeOH, RT 24h

* -J Org Chem, E.

MeHN Me

&C02R*

*

105, 5935 OMe

I

P h - CI - C 0 2 M e I

OMe

71 % (19841, 3,515

yo-Na+ 'Ph

T H F , O'C,

* R.O. : Maienfisch,

4h

1519

60%

J Am Chem Soc, (1983),

1 2 ' 5 1205

Cohen, M.J.: McNelis,

66,

"V

a - n a ph t h y 1

Ph C E C C 0 H

Duthaler.

~

CH2C1

* ; Raman,

&

RT

(19831,

* (81% e e R )

P. Helv Chim Acta, ( 1 984) , ---

60%

3, 845

SECTION 360


1.

EtO,

,OTMS

TMso/c=c'

OEt

CH2C12, 4 5 m i n

2 . MeOH,

61

, ZnC12

2N HC1,

RT

*

CC02Et

5 min

84%

Reetz, M.T.*; Heimbach, H.; Schwellnus, K. Tetrahedron Lett, (19841, 25, 51 1 1 . iPrfHCH20H,

0

It

PhCCH2C02H

2.

NH2 LDA, M e I ,

3.

LDA,

t

THF,

BnBr,

4. nBuOH,

heat -78°C

-8O"C,

1 0 % H2S04

reflux,

>

THF

PhC-C-CO2FBu I

Me

(S)

96h

50%

Meyers, A.I. ; Harre, M.; Garland, R. J Am Chem Soc, (19841, 106,1146 ----

\

0 U

1 . PhCHO, E u ( f o d ) 3 CH2C1

4

57%

Castellino, S.; Sims, J.J.


1 . LDA, EtC02CH2C02Et 2 . H30+ t

0°C

*

0

II

EtCCHC02Et I

OH 57%

Lee, S.D.: Chan, T.H. ; Kwon, K.S. Tetrahedron Lett, (19841, 25, 3399

SECTION 360

1

.

405

KETONE

(MeO) 2PCH, ,C02CMe2CC1 3 C02Me

L iN ( TMS )

nBuCHO

-

ESTER

2 . Z n ( d u s t ) , 25°C 3. HOH

0

I1

0°C

nBuCC02Me 66%

*

Horne, D . ; Gaudino, J.: Thompson, W.J. Tetrahedron Lett, (19841,

0

II

CH3CCHC02Me

I

Me

2 CH2=CHCH20Ac, 20°C nBu3P, THF

*

5% R h H ( P P h 3 ) 4

*

25,

Me I

93%


25,

5157

PhH

reflux, 21h Dunlap, N.K.:

&

C02Et

Sabol, M.R.:

*

Watt, D.S. Tetrahedron E ,(19841,

84%

3, 5839

(TMS)2S04 DCE,

80°C

~

Me

lh

(65

*

Morizawa, Y . ; Hiyama, T. ; Oshima, K.: Nozaki, H. Bull Chem Soc Jpn, (19841,

----

0

II

CH2=CHCH2-C-CMe I C02Me

T s u j i , J. ; Minami, I . ; Shirnizu, I.

Mn(OAo)3,

3529

35)

71 %

57, 1123


-

A C 0 2 E t

U

Pinkey,

Me

\

OMe

NPh CN

82%

* J.T.

1 . Me2C=C,

l

CH =C

t

24h

Kozyrod, R . P . ;

/

%

M e O e P b ( O A c ) 3 PyICHC13, 40°C

Org Syn, (1984),62, 24

10-

*

H30

1.

it

Me2CHCC1

THF

EtO, TMS 0

-78°C

,c=c,

S.-H.

1 . KH, C02Me

,OTMS

,

OEt 22"C,

0 II Me2CHCCC02Et I1 0 93%

ZnC12

4h

t

Tetrahedron Lett, (19851,26, 6333 DMSO,

2. Me2C(N02)2, 6h

*

Me


2. Ht

Reetz, M.T.

I

CH3CCH2-f'-C02Me

%

7 9%

CH2C12,

* ; Kyung,

Me

Ii

t

Ahlbrecht, H. ; Dietz, M.

0

,

OMe

-78°C 2 . M e I , THF, 3.

SECTION 360

0

15 min DMSO

C02Me

? & o * 86%

Kornblun, N. ; Kelly, W.J.; Kestner, M.M. --J Org Chem, (1985), 50, 4720

SECTION 360

-

ESTER

1 . LiA1H4,

THF

407

KETONE

0

*

2 . HC1, d i o x a n e

0

II

II

P hCH 2 C O C H 2 0 C P h

Ph

Naim, S.S.; Hussain, M.; Khan, N.H.

t'"u C02Me

2 Mn(OAc)3, 60°C,

64%

*


AcOH

CU(OAC)~ l h

-pr

C02Me

"%,,

75%

*

Snider, B.B. ; Mohan, R.: Kates, S.A. --J Org Chem, ( 1 9851, 50, 3659 P d C l 2( P P h 3 ) 2 ,

*ae

MeOH

NEt3,

600 psi C O

MeCN,

PhH,

24h

100°C(autoclave)

Tour, J.M.; Negishi, E. 0

C

0 II OCPh

CGCH

1.

* 2 Am

II

(PhC)20, CH,Cl,,

2 . O°C 3.

-

pH 7

Tanabe, Y.; Mukaiyama, T.

Chem SOC, (19851,

Ti(OTfI2 O°C

RT

84%

107, 8289

0 II -0CPh

C

C C H CPh II 2 II 0 0

Chem Lett, (19851, 673

87%


1. Zn/Cu,

I CH 2CH 2 C 0 2 E t

RT

Me2NAc,

-

PhH

SECTION 360

0

II

6OoC

EtCCH2CH2C02Et

2. Pd(PPh3)4, 5h 3 . CH CH C C 1 , 3 0 m i n 3 211 0

84%

Tamaru, Y.: Ochiai, h.; Nakamura, T.: Tsubaki, K.; Yoshida, Z. Tetrahedron Lett, (1985), 26, 5559 1. (cBu3Sn)20

2 PhCH2COOH

*

0

0

P h ! O C H 2 : o B r

2 . BrCH C o B r 211 -

0

60%

Vijayaraghavan, S.T.; Balasubramanian, T.R. -J Organofnet Chem, (1985), 282, 17

Os04, L B u O O H

PhCsCSiMe3

MeOH

0

It

t

PhCC02Me 61 %

Page, P.C.B.*; Rosenthal, S. Tetrahedron Lett, (1986), 3, 1947 1 . 2 Ph3P=CHC02Et

0

II

PhH,

EtOCH2CH2CC1

5OC-RT1 2 h

2. Al(Hg),

*

w e t THF

0

II

t EtCH2CH2CCH2C02Et 87%

Shchez, I .H. ; Larraza, M.I.; BreGa, F.K. ; Criiz, A. ; Sotelo, 0.; Flores, H.J. Couunm, (1986), 16,299

SECTION 361

ESTER

l o PhC, E t

100°C,

C-CH(CM2)4CH3

w

EtCCHnC5H1

I -

H

2

N

OAc

*

84%

Yamakawa, K . will Chem Soc Jpn, (19861, 59, 946 ----

n ii

t

C

DMSO

2 . a q . HC1

Satoh, T.; Motohashi, S.:

e

409

NITRILE

1 . CsOAc/Pb(OAc)4

/ \

/

-

M- e 3 0,CPh

II

PhCOCH 2 C P h

L

Thorat, M.: Mane, R.; Jagdale, M.; Salunkhe, M. Org Prep -Pnx? I n t , (1986), PhI, CO, CH3CH ( C 0 2 E t ) 2

Kobayashi, T.: Tanaka, M.

99%

2,203

;

12OoC, N E t 3

PdC12(dppf),

i

0

*

PhCCH2Br EtOH, 2h

y 2 E t PhC-C-CO2Et

33h

I

Me 75%

*


3, 4745

ec

Also via: Ketoacids (Section 320); Hydroxyketones (Section 330)

SECTION 361: Ester

CN OH

-

Nitrile

1 . LDA, 0

THF

- 2OoC, 12h

2 . A c O H-7OOC , THF

*

*

Milenkov, B.; Siisse, M . ; Hesse, M. Helv Chim Acta, (1983), ---

68,

51 %

21 15


SECTION 362

1 . KOH/EtOH

E m s t , A.B.:

Fristad, W.E.

50%

*

8%

-

-

Tetrahedron Lett, (1985), 26, 3761 CN

PhBr,

NECCH C 0 E t

Uno, M.;

LBuOK,

PdC12(PPh3)2,

5h 70°C

I

b

PhCHC02Et

7 3%

monoglyme Ueda, W.: Masuda, M . ;

Seto, K.;

Takahashi, S. Synthesis, (19851, 506

SECTION 362: Ester

-Olefin

This section contains syntheses of enol e s t e r s and e s t e r s of unsaturated acids.

, I

Shea, K . J . ;

E

4h Gilman, J.W.

Me2C=CHCH20H

Vatele, J.-M.

*


1 . KH 2.

^.

85%

F, c, = c, .Me Me0 S(O)Pi7

* 60°C

CH 2 = C - C 0 2 M e

I

M e - CCH = C H 2


I

Me

65%

SECTION 362

ESTER

-

t -

n B u 2 T e - C H C 0 2 E t , THF PhCHO -2OoC,

41 1

OLEFIN

l h

*

PhCH=CHC02Et

(E:I =* 5 0 : l )

*

75%

Osuka, A. ; Mori, Y.; Shimizu, H.; Suzuki, H. Tetrahedron =,(1983) , g!, 2599

Na2S, B~ Br

cat.

PhH/HOH (C8H17)3NMeC1 l h

88%

* Nakayama, J. ; Machida, H.:

Hoshino, M. Tetrahedron E,(1983) , 2, 3001

Aryal-Kaloustian, S . : Agosta, W.C. --J Org Chm, (19831,

48,

1718

81 % 1)

412

CI


NOz

SECTION 362

1. NaC(Et)(C02Et)2 HMPA

2 . NaBr,

,

hw

140"C,

3h 56%

*

Ono, N. ; Tamura, R . 4 Eto, H i ; Hamamoto, I . : Nakatsuka, T.; Hayami, J . ; K a j i , A. --J Org Chem, (1983), 48, 3674

,

1.

Ti(3iPr)4,

2 . LiAlH,,

boo

TiC14 -20°C

Et,O

25°C S 0 2 N iP r 2

3 . Cr03,

84%

a q . HC1

(88% ee R )

*

Oppolzer, W. ; Chapuis, C . ; Kelly, M.J. Helv Chim Acta, (19831, 66, 2358 Oppolzer, W.*' Chapuis, C - T m z n L e t t , (1%4), 3,5383 Oppolzer, W.": Chapuis, C . ; B e r n a r d i n e l l i , G. Tetrahedron Lett, (1 984) , 25, 5885

-

TMS-CH2CCH20Ac

nC 6 H 1 3 C H =CH C02Me (E)

dppe,

THF

P c ~ ( P P ~ ~ ) ~ , r e f 1 ux

Trost, B.M.*; Chan, D.M.T. T r o s t , B.M.

C02Me 51 %

---J Am Chem SOC, (1983), 105, 2315, 2326 * ; Balkovec, J.M.; Angle, S.R. Tetrahedron Lett, (1986), 27, 1445

SECTION 362

ESTER

Q

-

413

OLEFIN

Li I

&

C02Et

1 . Me2CC02Et, 8 p s i C O THF-HMPA, -78 25°C

-

2.

EtOS02F, - 7 8

-

25°C

"'C 0 E t

Fe ( C O ) 3

96%

a*

*

Semmelhack, M.F. ; Herndon, J.W.; Springer, J.P. J Am Chem Soc, ( 1 983), 105, 2497 ----

0,

0 II R OCCH=CH2

*

TiC12(0iPr)2

C02R

O C H 2t-B u

Oppolzer, W.

x

* : Chapuis, 1.

C.; Dupuis, D.: Cuo, M. Helv Chim Acta, (1983),

---

2100

C =Cr ( C O ) CH2=CH

PhH,

I

25"C, 1 .5h

C02Me

2 . D M S O , 3 . 5 h , 25°C

*

0

I1

68,

MeO,

Wulff, W.D. ; Yang, D.C.

PhCH=CHCH20COMe

Trost, B.M.

91 %

J Am Chem ----

71 % Soc, (19831,

NaCH(C02Me)2, T H F T H F , 1 5 % bpy 1 5 % (MeCN),W(CO), 4h

* ; Hung, M.-H.

J Am Chem Soc, ----

*

105,6726 CH=CH2

I

PhCHCHC02Me

I

C02Me

(19831,

105,

7757

91 %

SECTION 362


1. secBuLi, THF TMEDA, -78°C

0

II

CH3CH=CCNHMe

I

0 0 , THF -78°C-RT 3 . pH,3, r e f l u x Pattenden, G. Syn Commrn, (19841,

2*

CH3 Ladlow, M.;

4 0%

2,11

0 II

Et02CCC02Et, 180°C sealed tube, 72h Salornan, M.F.:

90%

* G.

Pardo, S.N.; Salornan, R 49, 2446 --J Org Chem, ( 9841, n

1 . MeLi, T H F , 1 . 5

:Me

0

THF/HOH,

* ; Lin,

Dieter, R.K.

CCBH17,

,H

c=c

’

Larock, R.C.

Y.J.;

54%

Dieter, J.W. (19841,

-J Org Chem,

$9, 3183

1 . Hg(OAc)2, T H F NaOAc, - 7 8 - 0°C n C 8 H 1 7CH=CHC02Me 2 . PdC12, LiCl MgO, MeOH, C O 80%

*

‘BO /B ‘0

24h

* : Narayanan,

-78OC K.

-

RT

(E : Z- = 9 8 : 2 )

J Org Chem, (19841, $9, 3411

SECTION 362

-

ESTER

415

OLEFIN

0

o v e r n i gh t t

L a r o c k , R.C.

c

; H a r r i s o n , L.W.; HSU, M.H. J Org Chem, (19841, ---

AcOH,

Pd(OAc)2,

L i O A> c

B g c k v a l l , J.-E.

d

*;

3, 3662

M e e o , ;

RT

\

7 6%

OAc

89%

( d l : m e s o = 6:4)

B y s t r i J m , S . E . ; Nordberg, R.E. J Org Chem, (1984), 3,4619 --C02Me

Mo ( C O ) * C P

M e 0 C/C'H

C02Me

Pearson, A . J .

/

* ; Khan,

C02tBu

C H =C

2

\

Me

CH2Br

Knochel, P . ; Normarit,

1 a. q K. O HTHF, , MeOH 20°C 2.

4 1 2 , MeCN,

M.N.I.

))I)) * J.F.

50°C

93 %

20°C

---J Am Chem

nBuCSCH, Z n THF,

Q$O

Soc, (1984),

*

C,

106,1872 02 t B u

CH =C

70%

\

CH2C=CH2 I nB u


25,

1475


N,

Cu(OTf)2, BnOH,

SECTION 362

reflux C02Bn

4h

63%

Smith 111, A.B.*; Toder, B.H. ; Branca, S.J. ---J Am Chem Soc, (19841,

106,3995

0 II L i O C C F 3 , CF3COOH 5% Pd(OAc)2,

RT

Ac OH

0qC 7F 5% 3

Backvall, J . - E .

Y

; Vagberg, J.: Nordberg, R.E. O

-


0

25, 271 7

CH2=CHCH2SiMe3

n

a

o

0 -=RT

t

Me30 BF4

CH =C HC H C HC H =CH C H CH C 0 Me

-

94h

85%

* Fujisawa, T. : Kawashima, M.;

Ando, S. Tetrahedron E ,(19841,

25,

321 3

1 . C H 2 = C ( , 0 E t ) 2 , PhH cat.

P hCH =CHCH 2 0 H

(L)

PdC12(COD)

0°C

-

RT

P hCH=CHCH 2 C H 2 C 0 2 E t

2 . PdC12( PPh3)2 x y l ene, 4h

r e f 1 ux

Ohshima, M. ; Murakami, M. ; Mukaiyama, T. -Chem Lett, (19841, 1535

86%

SECTION 362

ESTER

-

41 7

OLEFIN

0 II P h C H = C H C H 20COMe

dPPe P d 2 ( d ba )

* *

CHCl 91 %

dioxane, reflux

Tsuji,

* J. ; Takahashi,

K.: Minami, I.; Shirnizu, I. Tetrahedron Lett, (19841,

-

25, 4783

0""'

1 . 37% H C H O , PhSH, RT c a t . TMG, 2 4 h

*

2 . A c 2 0 , Py 3 . n B u 3 S n H , AIBN 80°C, P h H TMG = t e t r a m e t h y l g u a n i d i n e * Ono, N. ; Kamimura, A.; Kaji, A. Tetrahedron Lett, (19841,

80%

25, 5319

-

0

II

Ph3P=CHC02Et, N E t 3

CH3CH2CC1 CH2C12,

Lang, R.W.; Hansen, H.-J.

RT, lh

t

Org Syn, (19841,

T H F , CH3CH0 25OC, o v e r n i g h t

PhCH=C

\

C02Me

2 . HOH

* S.E. : Hoole,

MeCH=C=C" 'C02Et

62,

64%

202

Me

1 . LiA1H4, CrC13 ,CH 2Br

,,\"'H

*

o?$ 0

83%

Drewes, R.F.A. Syn Catgun, (19851, 2,1067 Okuda, Y.: Nakatsukasa, S.; Oshima, K. : Nozaki, H. Chem Lett, (19851, 481 --


f 6

C02Me CH2=CHC02Me, d p p e P d 2 ( d b a )3 'CHC1 DMSO, 8OoC, 2 h T s u j i , J.

Shirnizu, I . ; Ohashi, Y.;

CHCl,, J

* ; Boden,

*

26,

3825 0 II

18h

reflux

E.P.:

C02Me

C02Me 84%

4


0 II Ph3P=CHCSEt,

*

0"'";' 91 %

(E:I =

Mabury, S.A. Chem, (19851,

-J Org

96:4)

50,

709

6 N i ( C 0 ) 4 , DMF

CI

2.2 IPrOH 70"C, Hirao,

4 Me02C

C02Me

Keck, G.E.

SECTION 362

* T. ; Nagata,

C02Me

6h

S.; Agawa, T.


1 L D A , THF-HMPA -78°C 2 . a q . NH4C1

Harris, F.L.;

CH2=CHCH2CH2C02nPr

* Weiler, L.

61 %

26,

5795

C02Me

60%

JCS Chem Conm, (19851, 1124 T e t s e s @, (1984), 25, 1333

SECTION 362

ESTER

t

-

41 9

OLEFIN

-

Ph3As-CHCH=CHC02Et Et20,

2OO0C,

4h

85%

NOz

*

Huang, Y. ; Shen, Y.; Zheng, J.; Zhang, S. Synthesis, ( 19851, 57 OTf

CH2=CHC02Me,

DMF

2% Pd(PPh3)2C12

t-BU

3 NEt3,

wuco

* t-Bu

75OC

91 %

Scoti, W.J.; Peia, M.R.: Swgrd, K.; Stoessel, S.J. ; Stille, J.K. --J Org Chem, (19851, 2,2302 1. AcOH,

120'C

C1 CH2COOH

nC8H1 7CH=CH2

Mn ( OAc )

2. NaI, 3 . NE't3,

.HOH

*op

a c e t o n e nC8H1, THF

(1

Fristad, W.E. * ; Peterson, J.R.; Ernst, A.B. --J Org Chem, (19851,

0 OSiEt3

C02Et

+

CH = C H P P h 3 B r KF,

MeCN

+

0

3

ICCgH17 2) 72%

2,31 43

-w

C02Et 18-crown-6 80% r e f 1 ux Marino, J.P. ; Laborde, E. J Am Chem Soc, (19851, 107, 734

*


,OTMS

1 . CHC12Ph,

MeCH=C

(E:Z

'OE

MeLi

2 . PhCH3, h e a t

t

= 85:15)

Ph

/

*

MeCH =C'\

(E:I

C02Et

il-

P(OiPr)3

Pd(OAc)2,

nBuLi,

THF,

4 0 p s i C02,

RT

THF

95%

4h

*

T r o s t , B.M. ; Angle, S.R.

OH I

(CH2)7

i

CHO

7 9%

79~21)

Tetrahedron, (1985) , 41, 2643, 2653

Slougui , N . ; Rousseau, G.

Me

SECTION 362

---J Am Chem Soc,

B

1 . (Et0)2PCH2C02Et K2C03, HOH 20°C

2 . KOH, a q . E t O H , 30°C 3 . H 3 0t

m

(19851,

PH

(CH2)5

I

CH=CHC02H 77%

V i l l i e r a s , J.*; Rambaud, M.; Graff, M. Tetrahedron Lett, (19851, MeCHO, EtO-C=CCH2SiMe3 -60

-

107, 6123

26,

TiC14

53

/ CH2SiMe3

CH3CH=C 0°C

Pornet, J.; Khouz, B.; Miginiac, L. Tetrahedron Lett, (19851,

\

C02Et

7 0%

26,

1861

SECTION 362

ESTER

421

OLEFIN

oso Ph

0

"B u S n H

,,,,+CEC P h

AIBN

0 C S e- P h nII

Bathe,

-

PhH,

2h

*

M.D. ; Bosch, E.

OC02Me

I

cC6H13 - r - C

CH


P d ( d ba ) q C H C 1

PPh3,

* Tsuji, J. ; Suguira, T.;

15h

*

CH3

/

9 0%

3, 641

C=C=CHC02Me

f i C 6 H 13

99%


3, 731

MgS04

*

xyl e n e , r e f 1 ux

" Y O SePh II 0

\

Minami, I.

DBU,

Carling, R.W.;

MeOH

5 atm C O , 4OoC

CH3

t

(5

* Holmes, A.B.

p c c 5 H 1 1 0

52%

JCS Chem Cam, (1986) , 325

1 . BrCH2CC2Me, N a 2 T e

DMF, T H F , -20°C

PhCHO

2 . a q . H2S04

*

Suzuki, H. ; Inouye, M.

t

Chem Lett, (19861, 403

PhCH=CHC02Me 73%


E, 0

0

0

,

I

SECTION 362

Mn02, AcOH

5% P d ( O A c ) 2 , 42h

RT 7 0%

Antonsson, T.: Hemann, A . : Moberg, C. JCS Chem cosla, (1486), 518

---

-4

C02Me

D M F , 4ii s i e v e TBAF

*

66%

Majetich, G. ; Desmond Jr., R.W.: Soria, J.J. -J Org Chem, (19861, 51, 1753 0

1 . PhCHO B F3 * O E t 2 2. Ht

OMe

Tanaka,

* K. ; Yoda,

Ph

80%

H.: Isobe, Y.; Kaji, A . J Org C k m , (19861, C H 2 = C H CH 2 C 1

H C E C CH C H C OOH

*

*

2,1856 '

k

5

THF, PdC12(MeCN)2 RT,

5h

J Am Cheat Soc, ----

0

94%

Yanagihara, N.; Lambert, C . ; I r i t a n i , K . ; Utimoto, K.

H.

0

(19861,

* : Nozaki,

108,2753

SECTION 362

ESTER

EtCOOH, PhCH3,

HCECfiB u

-

EtKo m-Bu

4h 5,

+

1% R U ( ~ ~ C O D ) ~

c o

*

0 EtAo

72%

0

Mitsudo, T. ; Hori, Y.; Yamakawa, Y.; Watanabe, Y. Tetrahedron Lett, (19861,

BrCH2C02Et, nPrCHO -

100°C,

nBu3Sb

+

2.5h

BnOCC=CHiPr 1 CH3

Piva, 0 . ;

hv,

CH2C12

(-)-ephedrine -78"c

2, 2125

=CHC02E t

9.~ 2%


II

2%

*

nPrCH

Huang, Y.; Shen, Y.; Chen, C. 0

Jr""

0

PBu3 80°C,

423

OLEFIN

3, 2903 0

1 I

*

B n O C CI H C H = C M e 2 CH 3

71 %

(28% ee R )

* Henin, F.; Muzart, J.;'Pete, J.-P.

-

Tetrahedron Lett, (1 986),

27,

3001

PdCl 2(PhCN)2 0

s.J,

t Ph

Auburn, P.R.; Whelan, J.;

10 min

* Bosnich, B.

Organometallics, (1986),

"Yo Ph 95%

2, 1533


1. Br2

0 II M e 2 C =CH CCH

Engler, T.A.

CH3

I

*

CH2=C-CH=CHC02Me

2 . N a O M e , MeOH

* ; Falter,

SECTION 362

(L:L =

97:3)

*

Ph


W.

6

1. PhCHO, CH2C12 /CH S n C B u

CH2=C

\

4 BF3*0Et2

-

-78°C 2 . CF3COOH,

C02Et

Baldwin, J . E .

*

RT CH2C12


c

PhSeC1, NEt3

*

CH2C1 2 , -78OC dark

CH20H

Taylor, R.J.K.

* ; Caton,

Daub, G.W.

0

9 5%

M.P.L.

Tetrahedron E ,(19861, 3, 5919

E t C (OMe)3 ____.___)

'CH3

"-d

SePh

\

PhCH=C/

77%

RT, overnight ; Adlington, R.M.: Sweeney, J . B .

, '( C H 2 ) 3 C O O H

Huckstep, M.R.:

66%

125OC

* ; Shanklin, .H +

Ph 16)

Ph

(84

Tata, C. J Org Chem, (19861, 51, 3402

P.L.:

-

-

8 0%

SECTION 363

ETHER

-

ETHER

425

1. LiN(TMS)2

2. M e 3 S i C 1 Me,Siy

3.

CH2N2

4.

KH

+

C H 3 C H = C H C H =CHCO,Me L

%to, T.; Tsunekawa, H . ; Kohama, H.: Fujisawa, T. Chem Lett, (19861, 1553 --

*

83%

Review: IISynthes i s of a-Me thylene- Y- Lac tones"

Sarma, J . C . ;

Sharma, R.P.

Heterocycles, (19861, 24, 441

Related Methods: Protection of Aldehydes (Section 60A) ; Protection of Ketones (Section 180A) Also via: Acetylenic e st e rs (Section 306) ; Olef i n i c acids (Section 322; 6-hydroxyesters (Section 327)

SECTION 363: Ether, Epoxide, Thicether Thioether

- Ether,

Epoxide,

See Section 60A (Protection of Aldehydes) ad Section 180A (Protection of Ketones f o r reactions involving formation of Acetals and Ketals.

54 1

PO(0S i M e 3 )

*

Hujama, T. ; Obayashi, M.

78%


SECTION 363


6"

O\

CI C H 2 C H - C H 2 , RT

B u 4 N H S 0 4 , 3.5h

50% aq. NaOH

Mouzin, G.;

90%

Cousse, H.; Rieu, J.-P.; Duflos, A . Synthesis, (19831, 117 1 . THP-O(CH2)3CH0 2 . camphor-S03H

o P P II h 2

MeOH

0 Ley, S.V.

* : Lygo,

B.

-


H S i Et 2 M e 25"C, PhH, 3 h Murai, T.; Kato, N.

58%

0 s iE t 2 M e

(4

t

'+ " C H 2 0 S i E t 2 M e

* S.; Murai, S. ; Toki, T.; ---J Am Chem

Soc,

88% SuzuKi, S.; Sonoda,

(19841, 106,6093

1 . LBuLi, pentane/THF -78°C 2 . I(CH2)30SiMe2tBu T H F , -10 3. aq. H F

Amouroux, R.

?+

-

50°C

Heterocycles, ( 1 9841, 2, 1489

66%

SECTION 364

ETHER

-

HALIDE

SECTION 364: Ether, Epoxide, Thioether OH

- Halide, Sulfonate

1 . NaBr, 18-crown-6

RT, 5 min

CH2C12,

,,

2 . mcpba, 0°C 5 min Mechoulam, R.

Srebnik, M.:

427

*

80%

CH3CN,

0°C

*

&,

A ,

6

Melany, M.L.; Winstead, Thompson, Bunnelle, Thompson,

80%

J.; Harigaya, Y .

Tetrahedron Lett, (19841, --

1 . T i C H1 42 C, 1 - 4 5 ° C 2. MeOH, 3N HC1

Lock, G.A.;

\#”

H

0 Ts

* : Grote,

ooTs

b.

HO

12, NaHC03

Williams, D.R.

(19841, 1070

JCS Chem Cam, ---

CI %

25, 5231

f&

(97% ee)

9 5%

Thompson, D.W. Chem, (1985), 50, 3925 R.C.4 Simpson, T.H.; Lock, G.A.: Schiavelli, M.D.: D W J Org Chem, (19861, 51, 275 * Seamon, --W.H.,; D.W.; Mohler, D.L.; Ball, T.F.: D W. Tetrahedron Lett, (19841, 25, 2653

..

.

--J Org

428


CH30CH2COOH

Stadlwieser, J.

*

1. S0Cl2,

12OOC

2. A1C13,

80°C

\

CH30CH2C1

7 8%

Synthesis, (1985) , 490

,

Pb( OAc)4

\

w

SECTION 364

D M E , O"C,

ZnBr2

10 min

*

86%

*

Motohashi, S. ; Satomi, M.; Fujimoto, Y. : Tatsuno, T. Heterocycles, (1985), 23, 2035

THF,

*

*

Posner, C.H. ; Haines, S.R.

20 min

Tetrahedron E ,( 1 985) , 26, 5

12, N a H C 0 3 , Et20/HOH,

0°C

2h '

(I:E

Tamaru, Y.;

* Kawamura, S.; Yoshida, Z.

&.

b = 98:2)

-

Tetrahedron Lett, ( 1 985),

I

26, 2885

98%

SECTION 365

Purrington,

Review:

-

ETHER

* S.T. ; Correa,

429

KETONE

57% (19861, 51, 1080

2 9 e,

I.D.

"Organic Synthesis with a-Chlorosulf ides"

Dilworth, B.M.:

McKervey, M.A.


0

SEZTION 365: Ether, Epoxide, Thioether

Carless, H . A . J .

-

92,

3731

Ketone

69%

* ; Fekarurhobo,

G.K.

-

Tetrahedron Lett, ( 1 9 8 9 , 2$, 107

1. Ni(R)

Ph

2. H30

Curran, D.P.

* ; Singleton, 1 . LDA,

t

42%

D.H. Tetrahedron E,(1983) , 2, 2079

THF,

-8O'C

SCPr

2. To1 S02-SCPr -8O"C,

Scholz, D.

*

16h

83%

Liebigs Ann Chem, (19831, 259, 264 e s h Chem, (19831, 2,655 7


0

0 SiMe,

Sakurai,

PhCH(OMe)2,

CH2C1

SECTION 365

g

~

i

h

1 0 % M e 3 S i I , -35OC

* H. ; Sasaki,

87%

(erythro:threo

K.; Hosmi, A. --Bull Chem Soc

CoMe

e, (19831,

= 99:l)

56,

3195

OMe

TMSOY

PhCHO

Eu(fod)3,

Danishefsky,

CHC13

*

0

Ph 85%

* S. : Harvey, D.F.; Quallich, G.; Uang, B.J. -J Org C h m , (19841, 3, 392

0

I1

PhCH =CHC P h

(L)

0 c a t . H ( N H C H ItC ) l ONHBu hPr / -+ . . , " Ph

*

NaOH, H 2 0 2 , CC14 2-methyl butane,

Banfi, S.; Colonna,

H

76%

RT

(95% ee)

* S. ; Molinari,

*

H.; Julia, S. : Guixer, J. Tetrahedron, (19841, 110, 5207 1 . C O ~ ( C O ) ~R ,T

CH3C5CCH20CH2CH=CH2

2.

6ooc

24h

Billington, D.C.

* ; Willison,

D. Tetrahedron

* I

3 6%

E, (19841, 25, 4041

SECTION 365

-

ETHER

0 II CH2=CHCCH3,

6h

K-10 c l a y , Fe

*

Laszlo, P. ; L u c c h e t t i , J.

+3

65% (exo:endo = 0 . 6 : l )


Sn(OTf)2, -78

-

3, 4387

fiP

8

PhSCH2C02Me, C H 2 C 1 0°C

A

7 5%

N%N-TMS Shimizu, M.;

431

KETONE

Akiyama, T.; Mukaiyama, T.

Chem Lett, --

(1984), 1531

1 . ( C O C1l .)5, ,h P h H 2. NEt3, COOH S n i d e r , B.B.*(' S n i d e r , B.B.*f

M 'e t

PhH

r e f l u x , 2.5h

Me

66% a # e 7 % %Me

-

JOrg Chm, (1985), 50, 5167 Hui, R.A.H.F. Hui, R.A.H.F.; Kclkami, Y.S. 3 Am Chem Soc, (1985), 107, 2194 ---1 . (COCl)*, PhH R T , 3h r e f l u x , 6h

Brady, W.T.

* ; Giang,

Y.F.

J Org chepa, (19851,

60%

50,

5177


0

It

CH 2 O

CH3CCH3

nC5H1 S - N a Sabirov, S.S.:

SECTION 365

n C 5 H 1 1SCH2CH2CCH3 -

t

61 %

Gnevasheva, L.M.; Ismailov, M . I . ; Isobaev, M.D. J Org Chem USSR, (19841, 20, 1239 1 . KH,

THF,

-

-11 2. gl

.

HMPA

25OC

AcOH,

HOH

SPh

*

Cohen, T. ; Yu, L.-C.; Daniewski, W.M. J Org Chem, (1985), 1 . SnC12.2H20,

EtOH,

2.

ice

3.

pH 8

4.

l e v u l i n i c acid, 0.1N H C 1 ,

Varma, R.S.: Kabalka, G.W.

@@/Yh

*

'Ph

80°C 7 9%

>

2,443

(y;.

S ~ Conrmrn, I (1985),

c1 04-

4596

RT

3.5h

PhCH(OMe)2, CH2C12 -78OC

Mukaiyama, T.; Iwakiri, H.

50,

69%

86%

(=n:anti

= 88:12)

Chem L e t t , (19851, 1363

-

ETHER

SECTION 365

433

KETONE

PhCHO,

Me2AlCl

CH2C12,

-78OC

88%

*

Naruse, Y.: Ukai, J.: Ikeda, N.: Yamamoto, H. Chem Lett, (19851, 1451

--

1 . CH2=C,

,OSiMe

tBu 2-

/

0

II

*

T r C 1 0 4 ,P h C H 2 C 1 2 -78OC, l h

Me2C =CCH

2 . PhCHO,

OSi f P

h

y

-78OC

3. aq. NaHC03

MeCH=C,

S,

Ph Me

M e O H /CH,Cl,, L

Takeda, T.

91 %

Chem Lett, (19861, 221

Kobayashi, S . : Mukaiyama, T.

3t

,

TiC14

> L

-23°C

1 .5h

; Kaneko, Y.; Fujiwara, T.

0

II

Me2CHCCH2N02 HMPT,

Miyake,

87%

-


PhSH, A I B N

* H. ; Yamamura,

h

90°C,

3, 3029 0

>

I1

Me2CHCCH2SPh

2h

69%

K.

Bull Chem Soc Jpn, (19861,

2,89


1.

(Me0)2CHCH2CH2SnMe3 TMSOTf

*

2 . TiC14

$Me

3 . PDC

Lee, T.V.

SECTION 365

* : Richardson,

Taylor, D.A. Tetrahedron E ,(1986),

K.A.;

83%

3,5021

CH2C1

Pirrung,

* M.C. ; Werner,

2 Am

J.A.

9 5%

Chem

SOC,

(19861,

Ph

6h

57% Roskamp, E . J . ;

Johnson, C.R. 1.

OH21 OH

?4

---J Am Chem

17%

Soc, (19861,

108,6062 0

dioxane

5% Bu4NHS04,

6OoC

>

I1 E C 1 0H 2 1 O C H 2 C C H 3

2 . 1 % a q . H2S04, 60°C 71 %

dioxane

Gu, X.-P.:

bMe

( C 1 CH2)2CHOCH20Me NaOH, a q .

"1

108,6060

Ikeda, I . ; Kornada, S.; Masuyama, A , ; Okahara, M.

--J Org Chem,

(1986),

2,5425

*

SECTION 366

-

ETHER

NITRILE

SECTION 366: Ether, Epoxide, Thioether

-

435

Nitrile

Me3S i C N h

TiCl

HO'Me (95

CH2C1

Elliott, J.D.

* : Choi,

V.M.F.;

PhCH2CN

Makosza, M.

Bu4NBr, t

98%

5)

Johnson, W.S.

--J Org Chern,

iPrCHO,

HO

(19831, 48, 2294 0

50% NaOH 2OoC,

l h

/ \

t

Ph-C-CHiPr

1

; Kwast, A.; K w a s t , E.; Jonczyk, A.

-J Org C h m , TMS-CN,

( 1 9851,

Zn12

CH3CH(OMe)2 25OC,

CN

2,3722 CN

I

w

CH3CH OMe

15 min

63%

Kirchmeyer, S.; Mertens, A.: Arvanaghi, M . ; Olah, G.A. Synthesis, ( 19 8 3 , 498

0

M e 0 OMe

*

1 . LBuNrC, CH2C12,

-78

2. a q . NaHC03

-

O°C

*

CN

-0 Me0

TiC14

80%

*

I t o , Y. ; Imai, H.; Segoe, K.; SaeguSa, T. -Chem Lett, (19841, 937

92%


2 NaBH3CN,

cat.

20 tBuN=C,

tBuOH

,

r e f 1ux

nBu3SnC1

Stork,

BoEt

AIBN

t

“’CN

4h

* G. ; Sher,

60%

J Am Chem ----

P.M.

SECTION 367

(19861, 108, 303 (19831, 6765

105,

Soc, J Am Chem Soc,

----

SECTION 367: Ether, Epoxide, Thioether

-

Olefin

En01 ethers are found in this section. 0 II Ph2PCH(OEt)2

CH=C

>

(OE t ) 68%

van Schaik, T.A.M.;

8

-

2.2

nBuSCHCH2CH3

I

CH3

Miller,

HN(TMS)2,

2 TMS-I,

* R.D. ; McKean,

&

*

Henzen, A.V.; van der Gen, A. Tetrahedron Lett, (19831, 24, 1303

14h, 25°C

D.R. -

CH2C12

* EtCH=CHSCHCH2CH3

d5

(L:L=

67:33)

-

Tetrahedmn Lett, (19831, t

CH2=CHCH-AsPh3 THF,

-

*

-78’C-RT

Ousset, J.B.; Mioskowski, C.*; Solladie, G. Tetrahedron Lett, (19831,

-

81%

211, 2619

65%

2, 4419

SECTION 367

ETHER

PhCH3,

-

437

OLEFIN

7OoC, 6h

84%

Hartner Jr., F.W.: Schwartz, J.; Clift, S.M. J Am Chem Soc, (1983), ----

105, 640

,Si E t

0.1 Pd(PPh3l4

RT

CCl,,

95%

Stanton, S . A. ; Felrnan, S.W.; Parkhurst, C.S.; Codleski, S.A. J Am Chem Soc, (19831, 105, 1964 ----

*

OMe

0 II

PhCR'

. ,

Me?

CDC13, 4 8 h

0 . 5 '% E u ( f o d ) 3 R = OTMS, R '

* f4i R%0

= H

Bednarski, M.: Danishefsky, S.* ---J Am Chem Soc, (1983), R = H,

R ' = Me

1 0 KBar, 20h

Jurczak, J.; Colebiowski, A.; Bauer, T. /

OEt

(C0)4Fe=C

\

Ph

Ph

Semlhack, M.F.*:

82%

105, 3716

81%

(E:I =

1:l)

Synthesis, (19851, 928 Ph

CH2=CHPh,

5OoC

55 p s i COY l h

Tamura, R.

2

>

I

EtOCHCH=CHP h

60% Am Chem Soc, (1983),

(El

3, 6750

438 CCNPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6

O, M CH2=C=C

\

e

PhZnC1,

Ph

THF

2% P d ( P P h 3 ) 4

CMe2

I

SECTION 367

I

*

C H 2 = C - CI= C M e 2 OMe 9 5%

OAc

Kleijn, H.; Westmijze, H.; Meijer, J.; Vermeer, P. Rec Trav Chim Pays Bas, (19831, 102, 378 ---

Me

BF3*OEt2,

0

Et,

1\

/

C-CHSiMe2Ph

c

5 min

CH2C12,

* Fleming, I. ; Newton, T.W.

-78OC

t

Me

,C = C H O S i M e 2 P h /

68%

(-E :-Z

= 4:96)

JCS Perkin I, (19841, 119

tBu

-1

L iN-toc t y l

TMS-C1,

+ .

-78°C THF

Corey, E.J. * ; Gross, A.W.

(97.5

2.5)

:

-a

Tetrahedron=,

(19841,

25, 495

OSi!leEt2

HSiEt2Me,

PPh3

co2(co)8,

12OOC

50 a t m CO

0 s iM e E t

88%

*

Chatani, N.; Furukawa, H.; Kato, T.; Murai, S. ; Sonoda, N. J Am Chem Soc, (19841, 106,430 ----

SECTION 367

ETHER

-

4 39

OLEFIN

1 . H g ( O A c ) 2 , g l . AcOH

nu

RT, 30 m i n

CsCnPr 2 . NaBH4, NaOH 63%

*

---J Am Chem

Larock, R.C. ; Harrison, L.W.

Soc, (19841,

1 . i B u M g B r , E t 2 0 , 6h C p 2 T i C 1 2 , 0 - 25'C

T M S - C E C C H 0H

2 ' fic6H13hcH3 0 3 . B F 3 * 0 E t 2 , CH2C12

*

Sato, F. ; Kanbara, H.: Tanaka, Y.

90%

Tetrahedron Lett, (1984) ,

1 . 3 L D A , T H F , -1OOC

0 II P hSnB u

2 . TMS-C1,

-1 0

*

Miller, R.O. ; Hiissig, R.

-

-

25°C

25, 5063 PhS

b

\

/C=CHEt 8 0% (E:L = 2 : l ) Tetrahedron El(1984), 25, 5351

3 . a q . NaHC03

t

106,4218

TMS

1. nBuLi, THF HMPA 2. gCgHl9CHO 80%

*

Ousset, J.B.; Mioskowski, C. ; Yang, Y.-L.; Falck, J.R.

*

Tetrahedron Lett , ( 1 984) , 25, 5903

8"'


6

1 . LiCHPh(OMe), 2.

RT

CS2,

3. MeI,

-

THF,

reflux

reflux

*

4 . nBu3SnH, AIBN reflux,

Vatele, J.-M.

*

n

-78°C

PhH

-


SECTION 367

62%

(I:r = 4:6) 25, 5997

pTsOH * H O H PhH,

18h

~

r e f 1ux (Dean S t a r k )

*

Nickon, A. ; Rodriguez, A.D.;

do

-

e

,

S h i r h a t t i , V.;

,

(1985),

cat.

*

nBu3SnOPh, THF

CH3CH=CHCHnPr

Keinan,

* E. ; Sahai,

Pd( PPh3)4, M.;

RT

82%

87%

(111)

T o r i i , S. ; Inokuchi, T . ; Yukawa, T. --J Org Chem, (1985),

I

4218

NaOH

= chloropyridine cobaloxime

OA c

Ganguly, R.

50,

E t 4 N O T s , MeOH

L - E t

cat.

60°C,

67%

50,

5875 OPh I

>

CH3CH=CHCHnPr Ph

p

t

C H CH C H = CHcPr

*

Roth, Z.; Nudelman, A. ; Herzig, J. J Org Chem, (1985), 50, 3558

S E C T I O N 367

-

ETHER

OLEFIN

441

0

0 SiMe, (CO)5MnSiMe3, RT,

CD3CN

3h

88%

Marsi, M.; Brinkman, K.C.; Gladysz, J . A .

Lisensky, C . A . ;

--J Org

Vaughn, G.D.;

50, 3396

Chem, (19851,

OM e

2C5H11, Me

/

c =c

/

C H =C HC

2. BnBr

NMePh

I

BnCCH 2CH2CHCH3

92%

3 . H30t

*

Ahlbrecht, H. ; I b e , M.

CN

II

I

CN

SECTION 374


*

Nikishin, C . I . ; Troyansky, E . I . : Misintsev, V.V.; Molokanov, A.N.; Ogibin, Y.N. Tetrahedron G,(1 9861, 3, 421 5 SECTION

374: Ketone - Olefin -

For the oxidation of a l l y l i c alcohols t o olefinic ketones, see Section 168 (Ketones from Alcohols and Phenols). For the oxidation of a l l y l i c methylene groups (C=C-CH, + , see Section 170 (Ketones from A l k y l s ad Methylenes).

C=C-CO)

For the alkylation of olefinic ketones, see also Section 177 (Ketones from Ketones), and Section 74E ( A l k y l s from Olefins) f o r conjugate alkylations. 1 . PhSC1, 2. NEt3,

McKervey, M.A.

Et20,

0°C

>

&SPh

RT, o v e r n i g h t

* ; Ratananukul,

P.


75%

2, 11 7

SECTION 374

Br

KETONE

0 II HP(OEt)2, NEt3,

-

OLEFIN

465

RT

15h

(96

* Hirao, T. ; Masunga, T.;Hayashi,

K.;

4)

:

66%

* Ohshiro, Y. ; Agawa, T.


0 O C C l , l h O, M

e

CH 2 = C \ SnMe3

Pd (Bn) ( PPh3 )2C1

*

q ) j - O M e

Soderquist, J . A . ; Leong, W.W.H.

Tetrahedron E,( 1 9831,

TMSo

86%

2,2361

OMe SnC14,

OTMS

Nakamura, E.; SiMe, 1

0°C

CH2C1

* Shimada, J.; Kuwaji'ma, I. JCS Chem Cam, (19831, ---

60%

498

*

Nakamura, E.; Fukuzaki, K.; Kuwajima, I.

J C S Chem C a m , (19831, ---

499


OM e

I MeC(CH2)3C02Me I OMe

0 1 I CH2=CHCHCH2C(CH2)3C02Me

1

EtCOOH

Ph

* : Lunt, S.R.

+

( 1 2)

0

II CH2=CHCHCHCCH CH2C02Me 1 (88) 69% Ph

120°C

I

24h

Daub, G.W.

SECTION 374


1 % RuC13*H20 2 30% H202,

RT

0

5h

* 90% Ito, S.; Aihara, K.; Matsumoto, M. Tetrahedron Lett, (19831, 24, 5249 2 [ c 1 c u I IO - C U I ' c 1 ]

t-Bu&-BU

*

MeCN

Capdevielle, P.: Maumy, M.

Tetrahedron=,

OTMS

t*Bu6 0

80%

(19831, 24, 5611 0

1 % Pd(OAc)2, dppe MeCN, r e f l u x l h 78%

Tsuji, J.*: Minami, I.; Shimizu, I. Tetrahedron

E, (19831, 24,

5635

SECTION 374

-

KETONE

0 II 1. i P r C C l ,

CH2C12

[ Z n / C u C l /CH2C1 2 / M e I ] 20°C

-

reflux

2 . 1M K O H , MeOH

OLEFIN

4 67

* @ 7 5%

*

Shono, T. ; Nishiguchi, I.; Sasaki, M.: Ikeda, H.; Kurita, M. J Org Chem, (19831, 48, 2503 ---

-

0 '02,

Ac20,

DMAP

Py, CH2C12,

Mihelich,

*

2h

* E.D. ; Eickhoff , D.J.

71 %

J Org

-

M e 2 C = C H B r , PhCH3

/OAC CH2=C \ Ph

PdCl 2 ( g T o l 3 P ) 2 Bu3SnOMe,

,

(19831,

Kosugi, M.; Hagiwara, I.; Migita,

II

PhCCH2CH=CMe2

* -T. Chem L e t t ,

MeCH=CHLi,

2h

Pet ether,

-3OOC

74%

(19831, 839

78%

*

Mukaiyama, T. ; Ohsumi, T.

-Chem L e t t ,

4135

0

100°C

30 m i n

48,

(1983), 875


1. EBuLi

0

2 . ZnC12, THF C H =C =CH OMe

R u s s e l l , C.E.;

t

II

3 . T o l - I , RT, 8 h PdC12(PPh3)2, D i b a l - H

4. aq. H Hegedus, L.S.

3h

________)

RT

-

reflux

CH2C1

-

NEt3,

*

Negishi, E. ; Miller, J . A .

0

II

MeCH=CHCCl

66%

J Am Chem Soc, (19831, _105, 943

2 EtA1C12, b i M e ,

C H 2 =CHC - TO1

t

*

SECTION 374

97%

THF, 6OoC 24h

---J Am Chem

54% Soc,

CH2=CHSiMe3,

CC14

A1C13,

30 min

50°C,

(1983),

105,6761

-4

K j e l d s g n , C.; Knudsen, J.S.; Ravn-Petersen, L.S.; T o r s s e l l , K.B.C. Tetrahedron, ( 1 983), 3, 2237

63%

SECTION 374

-

KETONE

6% Pd(PPh3)4, THF,

OLEFIN

469

3% dppe

h

RT, 4 h

Y t-Bu

*

Trost, B.M. ; S e l f , C.R.

y

S

i

M

e

,

1

--J Org

.

2 LDA,

65OC

2 . CC14,

77OC

*

p."

AcO

g H 1 1)

* Rautenstrauch, V.

0

l h

-J Org

Wilson, S.R. ; Price, M.F.

84%

2, 722

Chem, (19841,

P d C 1 2 ( M e C N ) 2 , MeCN AcOH,

2, 468

THF

-

-70

YYo 0 0

Chem, (19841,

bl%

*

8OoC

J Org Chem, (1984),

9, 950

73%

0

II CH3C-Co(C0)3

*

- C H 2 N 02, TH F / D M S O

8h

* Hegedus, L.S. ; P e r r y ,

R.J.

A

0

54% --J Org Chem, (1984), 9, 2570


SECTION 374

-Jr

0 II 1 . MeOCH=CHCCH3, E t 2 0 R T , 24h 2. HOCH2CH2NH2,

I C g H 13

Molander, C.A.:

lh

*

c a t . C r ( C 0 ) 6 , 38h

tBuOOH, ref1 ux CH2C02Me

Pearson, A.J.

*

ICgH13

98%

Singarem, B.; Brown, H.C. J Org Chem, (1984), 49, 5024 ---

PhH

*Q

CH2C02Me

: Chen, Y.-S.:

HSU, S.-Y.; Ray, T. Tetrahedron L e t t , (19841,

" " 2 & 3

3KH

*

To1O2S3

7 5%

524

25, 1235

1 4 LiC1, DMSO 5OoC, 7 5 min

Denmark, S.E.

* : Harmata, M.A.

87%


25, 1543

1 . Me2CuLi, T H F

EtO

WoEt

-78"C, l h

3 . MeCNYre.f l u x

Marsi, M.; Rosenblum, M.

*

J Am Chem ----

52% Soc, (19841, 106, 7264

SECTION 374

e>

KETONE

-

471

OLEFIN

1 . Ts-CH2N=C

2 . LBuOK 3. BnBr

*

.

4 . H30t

53% Moskal, J . ; van Leusen, A.M. Tetrahedron Lett, (1984), 25, 2585 P h v HQC' N

0

Gordon, E.M. Sundeen, J.

N E t 3 / PhH

0

* ; P l u ~ ~ e J. c , ; Delaney,

90%

N.G. ; Natarajan, S. :

Tetrahedron g , (1984), 25, 3277 1. PhI,

nBuCZCH

0

0

26OC

CO,

Zn(Cu)

P d ( P P h 3 ) 2 C 1 2 , DME C p 2 T i C 1 2 , 6OoC, 4 h

0

*

II

P h C C H = CHnB u

2 . HOH

92% $4

Tamaru, Y.; Ochiai, H.; Yoshida, Z. Tetrahedron Lett, (19841, 3, 3861 1. K CO

-

-

BnC1, a c e t o n e 3'ref~ux

2 . 5 0 % a q . NaOH HOH/ E t 2O

k

P

Beraldi, P.G.: Barco, A , ; Benetti, S.; Pollini, G.P.:

V.

-

h 50%

Zanirato,


SECTION 374


C02CH2CH=CH2

MO(CO)~ PhCH3, r e f 1 u x 85%

*

Tsuji, J. ; Minami, I.; Shimizu, I. 1 . Pb(OAc)4,

Chem Lett, (19841, 1721

L n

PhH

reflux,

5 min t 2 . a q . NaHC03 1N HC1

3.

Nakatani, K.: Isoe, S.

*

69%


1 . Me3SiCH2CH=CH2,

0

TiC14,

Ii

-40°C

0

CH2C12, 3 0 m i n

PhCH =CHCCH3 2 . HOH,

-4OOC

-

RT

II * PhCHCH2CCH3

1

CH2CH=CH2

80%

*

25, 5335

Sakurai, H. ; Hosomi, A . ; Hayashi, J.

Org Syn, (1984),

62,

86

Me3SnCH2CH=CH2, 25OC 0 6 a t m C O Y PPh3 II Me2C=CHCH2C1 tMe2C=CHCH2CCH2CH=CH2 1% PdC12(MeCN)2 CHC13,

48h

*

54%

Merrifield, J.H.; Godschalx, J.P.; Stille, J.K. organanetallics, (19841,

3,

1108

-

KETONE

SECTION 374

PhCH3,

Macomber, D.W.

*

100°C

Ph

Organometallics, (1984),

bBr

Ce13,

THF

PhCHO,

*

473

OLEFIN

RT,

3,

64%

1589

t

l h

90%

Fukuzawa, S. ; Fujinami, T.; Sakai, S. JCS Chem Comn, (19851, 777

---

-

1. nBu3Sn-CEC-SiMe3, 0

PdCl 2 ( PPh3 ) 2 , r e f 1 u x

II

nC6H1 3CC1

DCE

2 . THF, 3.

RT,

620"C,

6h

14 Torr

*

56%

Ackroyd, J.; Karpf, M.; Dreiding, A.S. Helv C h i m Acta, (19851,

---

R

CH3CCH=CH2

1. P h S e - B a PhCH3,

25"C, 2h

2.

iPrCHO

3.

Py, H 2 0 2 ,

0

-

0

*

II

338

OH

I

C H 3 C - CI t - C H i P r CH2

30°C

* -J Org Chem,

Leonard, W.R.; Livinghouse, T.

68,

71%

(19851,

50, 730


474

SECTION 374

0

II

EtCCHC02Me, CH = C

2 \

C ,H

I

Me

3

30°C

Me

C02Me

1 ,

I

CH2=CCH2-C-Cq

-

Et

P d 2 ( d b a ) CHC 1 M' e 0 92% II 12 min * o T s u j i , J. ; Shimizu, I . ; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J Org Chem, (19851, 50, 1523 CH20COMe

-

-

1 . C1CH=CHC02H, OH

THF,

1

n 8 u C H C H =CH

65OC,

2 NaH

4h

2 . H 3 0t

*

0

II

nBuCH=CHCH2CH2CCH3

2 KH, 1 2 0 ° C * 6h Buchi, G. ; Vogel, D.E. J Org Chem, (19851, 3.

Negishi,

* E. ; Holmes,

OYP

58%

4664

62% S.J.; Tour, J.M.; Miller, J . A . ---J Am Chem Soc, (19851, 107, 2568

CH2=CHCH2Ti(NEt2)3 THF,

50,

-25OC,

15h

0

t

Ii

P hCCH 2CH = C H 2

95% Reetz, M.T.*;

Wenderoth, B. ; Urz, R . Chem Ber, (19851, --

e, 348

SECTION 374

-

KETONE

475

OLEFIN

tBuOOH, MeCN Cr(CO) r e f 1ux

Me C 0 2 M e Pearson, A . J .

* : Chen,

Me

C02Me

60%

Y.-S.; Han, G.R.; HSU, S.-Y.; Ray, T. JCS Perkin I , (19851, 267 ---

1. LDA,

THF

*

2.

12 BF3*OEt2

3.

5% Pd(PPh3)4,

CH2=CHCMe2N02, x

THF

"s"'/' 7 0%

RT

*

Ono, N. ; Hamamoto, I . ; Kaji, A. Bull Chem Soc Jpn, (19851, 58, 1863

----

cH

-

/

= c H C'H

HRh( PPh3)4,

0

- c H zc \

H

PhH,

105°C

*

0 18h II t CH3CH=CHCnC,H,

Sato, S.; Matsuda, I. ; Izumi, Y. Tetrahedron Lett, ( 1 9851,

-

8 CAN,

x

83%

26,

1527

25°C

5 0 % a q . MeCN

SiMe,

-

66%

Wilson, S.R. ; Zucker, P . A . ; Kim, C.-W.: Villa, C.A. Tetrahedron Lett, (1985), 26, 1969

476 CCMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6

SECTION 374

1. 2 nBu3SnCH2Li / 0 \ nPrCH-CHCCH3 -

*

I0I

THF,

-

-78°C

RT

nPrCH=CHCH2CCH3

2 . BF3-0Et2

Sato, T. ; Kikuchi, T.; Sootme, N.; Murayama, E. Tetrahedron Lett, (19851,

7 6%

26, 2205

PdCL2(PhCN)2 THF,

Clark,

* G.R. ; Thiensathit,

PH

OEt

I

nBuC5cCH-C-CH3

I

OEt

CH2C12,

CuBr, 3. Si02

2, 2503

NEt3

0°C

2 . 4 E t M g B r , THF

Bernard, D.; Doritheau, 0

67%

S. Tetrahedron Lett, ( 1 9851,

1 . MeS02C1,

II

t

reflux 2.5d

-30°C

nBu

*

-

E t

\

/

0

II

C =C=CHCCH3

68%

* A.

Tetrahedron L e t t , (1985), 26, 4923

-

0

C H I 2 - Z n Me3A 1

C H ~ C ( C H ~ ) ~ C H O THF,

25"C,

48h

I1

tC H ~ C ( C H ~ ) ~ C H = C H ~

* K. ; Nozaki,

Okazoe, T.; Hibino, J.; Takai, H. Tetrahedron L e t t , (1985),

96%

2, 5581

SECTION 374

KETONE

-

OLEFIN

477

MeCH=CHBr, C O Y 80°C P d ( P P h 3 I 4 , cBuOH 8h

Amari, E.; Catellani, M . ; Chiusoli, G.P. -J Organomet Chem, (1985) ,

-

0

0

I1

CH C H C C H C H 3 31 I Br Br

dioxane,

- Go

30 m i n

I))))

*

Joshi, N.N.; Hoffmann, H.M.R. Tetrahedron L e t t , (19861, 1 . 2 NaH,

II

2.

Ph3P=CHCC02Et

THF

CH2=CH(CH2)8CH0 cat.

2 . H30

Pietrusiewicz, K.M.*;

+

9, 383

, Zn/Cu, 10°C

TMS-C1

0

89%

HOH,

40°C

,I

(L:E

90%

P

3, 687 C02Et

(CH2)*CH=CH2

73%

= 9:l)

Monkiewicz, J. Tetrahedron L e t t , (19861,

27, 739

C H 2 = C H C H 2 0 A c , PhH

a z o o , Tsuda,

cat.

* T. ; Okada,

Pd(PPh3)4, 3h

RT)

* T.

M.; Nishi, S.; SaeguSa, -J Org Chem, (1986) , 2,421

93%


N a C H ( A c ) 2 , THF, 1 9 h

PhfHCH=CHPh

TiC,H,PdCl/L.

nn,

40°C

't

P h C H C H = CHPh

I

Hayashi, T , = ; Yamarmto, A. : Higihara, T.; I t o , Y. T e t r a h e d r o n L e t t , (1986),

-

Si02,

3, 191

sealed tube

60°C, 4h

*

SECTION 374

Me

HO

74%

Smit, W.A. ; Gybin, A.S.; Shashkov, A . S . ; gtrychkov, Y.T.: Kyz'mina, L.G.; Mikaelian, G.S.; Caple, R. ; Swanson, E.D. T e t r a h e d r o n Lett, (19861, 3, 1241, 1245

-

OH

I

CH2=CHCH20C02Me

CH2=CH(CH2)3CHCH=CH2 -CH2=CH(CH2)3CCH=CH2 R u H ~ ( P P ~ ~ ) ~ PhCH3, r e f l u x * Minami, I . ; Yamada, M.; T s u j i , J. T e t r a h e d r o n Lett, (1986),

-

1 . KH(12 p r e t r e a t e d ) 1 8 - c r o w n - 6 , THF _.____)

r e f l u x , 2h

apr 95%

3, 1805

2 . E t O H , -78°C 7 5% (improved procedure) * Macdonald, T.L. ; Natalie Jr., K.J.; Prasad, G.; Sawyer, J.S. JOrg-, (19861, 51, 1124

KETONE

SECTION 374

-

479

OLEFIN

0

I1 PhCCHN2, BF3*0Et2

MeCH = C H C H O H

RT,

Kachinsky, J.L.C.;

4h

* Salomon, R.G.

0

+

Hatanaka, Y.; Kuwajima, I.

i

k:H

I

Me -J Org Chem, (1986),

4h t

II

PhCCHCH=CH2 83%

51,

1393

63%

J Org Chm, -

(1986),

51,

1932

1. CH3CCH2CH2CHPhCOOH

2.

Ph

H

r e f l u x , 16h

LDA,

THF, -78°C

3 . Me1 4 , Red-A1 5 . Ht

Meyers, A . I .

t# 0

PhH,

t

Me

42%

(99.8% ee)

; Lefker, B.A.; Wanner, K.Th.; Aitken, R.A. -JOrg Chm, (1986), 51, 1936

-

OAC 1

C02CH2CH=CH2

?4

P d 2 ( d b a ) 3 .CHC1

PPh3,

CH3CN

t

Tsuji, J. ; Nisar, M.: Minami, I. Tetrahedron Lett, (19861, 3, 2483

480 COMPEM>IUM OF ORGANIC SYNTHETIC METHODS VOL 6

0 It CH2=CHCH20COCH2CH=CH2 (51e3

5% Pd(OAc)2,

*

5% dppe

MeCN,

30h

Minami,.I.; Takahashi, K.; Shimizu, I.; Kimura, T.

SECTION 374

Q

95%

-J w hJw Tetrahedron, (1.9861,

42,

2971

1 . LiN(TMS)2

2. 3.

PhCHO Me3SiC1

4.

5OOOC

Ph

hSiMe,

0

OSiMe,

2)

( 98

-


Bloch, R.; Gilbert, L.

1. tBuMe2SiOTf, -78OC PhCHO,

-78OC

-

RT

4 . HF, T H F / h e x a n e ,

* Kozikowski, A.P. ; Jung, 0

II

0°C

63%

J Org ---

S.H. 0 It

P h T l ( OCCF3)2

,

4% Li2PdC14,

*

PhCH=CHCCH3

25OC

1 .5h

J Org Chem, ---

-

Chem, (19861, 51, 3400

THF

5 CH3CCH=CH2

* Kjonaas, R.A.

3511

4,,

PPh3

2 . E B u L i , THF/hexane 3.

66%

27,

(19861,

51, 3708

98%

NITRILE

SECTION 376

-

48 1

OLEFIN

Reviews:

"Chromium (11) Reagents: Reduction of a-Acetylenic Ketones to trans-Enones"

*

Smith 111, A.B. ; Levenberg, P.A.: Suits, J.Z. Synthesis, ( 1986) 1 84

"Oxidation of Alkenes: Metal Induced Formation of an Allylic Carbon- Oxygen Bond"

Muzart, J.

*

Bull Chem Soc Fr, ----

SECTION 375: Nitrile

(19861, I165

- Nitrile

1 . L D A , P h H , 5"C, 1 5 m i n

NC

Br

3. H O H Br 4. 1 0 X p q . N a O H Davis, W.A.; Cava, M.P. --J Org Chem, (19831, 48, 2774

91 %

NC V C N

I

NaCH(CN)2y

CuI

HMPA, 12OOC

Suzuki,

* H. ; Kobayashi,

SECTION 376: Nitrile

-

T.; Osuka,

* -A. Chem Lett,

59%

(19831, 589

Olefin

*

Nishiyama, H.: Sakuta, K.; Osaka, N.; Itoh, K. Tetrahedron Lett, ( 1983)

2, 4021


0 CHO

1 . Me,C=C=NS

TMS'

TiC14,

SCN

iMe3

Ti(OiPr)4

CH2C1 -78OC 2. aq. Na2C03 3. B F 3 . O E t 2 , Okada, H.; Matsuda, I. ; Izumi,

Q

66%

2 y

1. LiCMe2CN,

-78

-

= 9:l)

(1983), 97

THF/HMPA 25°C

2 . CF3COOH, -78°C 30 m i n

* 85%

*

Semmelhack, M.F. ; Herndon, J.W. Organometallics, ( 1 983), 1. C02, Ca(OC1)2 CH2C12, HOH, 1 0 ° C 2. NaCN

3. B u 4 N I , HOH, l l O ° C 4. LBuOK, THF, RT

*

2,

363

- I'"

Suzuki, S. ; Fujita, Y.; Nishida, T. -Syn Comnun, (19841, 1

SECTION 376

FI

58%

fi, 817 CN

(Et0)2PCN, LiCN THF, RT, 5 m i n ~7

2. BF3*OEt2, PhH RT, 2 h

Harusawa, S.; Yoneda, R.;

* Kurihara, T. ; Hamada, Y.;


80%

Shioiri, T.

2,427

SECTION 376

NITRILE

1. PhCH2Br,

-

483

OLEFIN

K2C03

acetone 2 . 5 % a q . NaOH

e

CH2=C

/

\

CH2Ph CN 50%

Baraldi, P.G.; Pollinj., G.P.; Zanirato, V . ; Barco, A . ; B e n e t t i ,

s.

0


C S CH

OMe

Chatani,

TMS-CN , P'dC1 P y , PhCH3, r e f l u x 20h

* N. : Hanaf'usa,

T.

NC

'

c=c \

SiMe3

88% JCS Chem Comn, (1985), 838 ---

Me3S i C H 2 C H = C H 2

h v , MeCN, 4 0 h

66%

CN

Mizuno, K .

* : Ikeda,

M.:

*

O t s u j i , Y. Tetrahedron L e t t , (19851,

26,

461

Pd2(dba)3.CHC1 C02CH2CH=CH2

PPh3,

EtCN,

3h 81 %

r e f 1 ux

*

Minarni, I . ; Yuhara, M.; Shimizu, I . ; T s u j i , J. JCS Chem Comn, (19861, 118 ---

r


Miyake,

SECTION 377

R +FN CN

C02Me

TMS-CN,

RT

C02Me

______)

SnC14,

30 m i n

(2

CH2C1

* H. ; Yamamura,

CH2=CHCH2S i P h 3

C02Me

7

1 . PhCH=CHN02, T i C 1 4 C H 2 C 1 2 y -1 5 ° C 2. Zn, THF,

*

3,3025


K.

Uno, H. ; F u j i k i , S.; Suzuki, H.

65%

8,

CN

I

CH2=CHCH2CHPh

l h

*

6 9%

(1986) , 59, 1267

Bull Chem Soc JJJ, ---

- Olefin ---

SECTION 377: Olefin

1 . CBuLi, THF 78 " C

-

* CH2 CHCH=CHnC5H1

2. cC5H111 3 . 6 5 0 " C , 0.1 T o r r

Ls02

90%

Bloch. . . , R.:. Abecassis. J.: Hasson, D. .Can J Chem, (1984), 62, 2019 --Tetrahedron Lett, n 9 8 3 1 , Bloch, R . ; Abecassis, J.

2,1247

-

1. 2 LBuLi, hexane, CH2 =CHOE t

2 TMEDA -78°C

2 * ZnC12s T H F y -78-0"c

OEt

(L)

3 * ICH=CHnC5H1 5% P d ( P P h 3 ) 4 Negishi, E.*; Luo,

F.-T.

--J Org

I

CH2=C-CH=CHnC5H11 74%

Chem, (19831,

48,

1560

OLEFIN

SECTION 377

TMSO( CH 2 ) 6CECH

-

2 . aa. NaOH

3. E t C H = C H I

OLEFIN

485

H O ( CH2) 6CH = C H C H = C H E t

Pd ( P P h 3 )4 in PhCH 120°C 74% i n T H F 3: 65°C 74% Cassani, G . ; Massardo, P.; Piccardi, P .

(EE:ZE

=

99:i)

( E : E= 9 9 : l ) Tetrahedron Lett, ( 1 9 8 3 , 24, 251 3

n,

nC8H1 7 C H = C H ( CH2)7C02Me Villemin, D .

*

Me02(CH2)7CH=CH 1

______t

WCl,,u 80°C nC8H,, CH =CH S n M e 4 , 1 8 h 68% Tetrahedron Lett, (19831, 24, 2855 tBu

54%

t

CFCl

(77% eel Y Sakane, S.; Fujiwara, J . ; Maruoka, K.; Yamamoto, H. J Am Chem Soc, (19831, 2,6154 ---CHO

PI H

CH2=CHCHnC5H, CI

Pd(acac)*, PPh3* dioxane, reflux

* 70h Moreno-MGas, M. ; T r i u s , A. Bull Chem Sac Jpn, (1983), --

56,

2154


6

-6

1 . B r C H 2 S 0 2 B r , h v , - 1 5°C CH2C12, 2h 2 . N E t 3 , CH2C12, r e f l u x 3. L B u O K , T H F / t B u O H 0°C

* Block, E.*;

SECTION 377

74%

J Am Chem Soc, (1983), 105,6165 Aslam, M. Block, E . ; Eswarakrishnan, V. ; Gebreyes, K. Tetrahedron Lett, ( 1 9841, 25, 5469

_---

Me2C=CH)2CuLi

9

5

>-J

~ C 5 H l l E t 20/TH F 5% Pd(PPh3)4

1

*

Jabri, N. ; Alexakis, A.; Normant, J.F.

c

Hl + 1 2 5 H 11

/ (97

Bull Chem Soc Fr, ----

:

f

3)

94%

( 1 983) , 11321

CSC(CH2)3CH=CH2 1 . i s o o c t a n e

C Z C - TMS

cPco(co)6 r e f l u x , 97h

2 .CuCl - H O H N E t 3 , MeCN * Sternberg, E.D.; Vollhardt, K.P.C. --J Org Chem, (19841,

0 I

C02Me

CH2=CHCH=CHMe,

3,1564

-0

CH=CHCH=CHMe

NEt3

Pd(OAcI2, 100°C P ( g T o 1 )3, 1 5 h

SiMe,

71 %

C02Me (EE:EZ = 8:2)

- *Mitsudo, T.; Fischetti, W.; Heck, R.F. J Org Chem, ---

(19841,

3,1640

71 %

SECTION 377

OLEFIN

0

-

n C 7 H , 5MgBr

I1

CH2=C=CHCH20P(OEt)2

j

T H F , -25OC

*

487

OLEFIN

Ei7H1 5 C H 2 = C CH =CH

-

80%

Djahanbini, D. ; Cozes, B.; &re, J.

Tetrahedron, (19841, 40, 3645 L e t t , (1 984), 25, 203 Tetrahedron -

0-4 t h KFe- 1111 0 c l a0 °yC

\

t b u t y l phenol

lh

Laszlo,

* P. ; Lucchetti,

ECMe (CH2)4

Tetrahedron Lett, (19841, I _

25, 1567

Ph2PMe, - 2 0 ° C

I

C S C Me

4\

J.

77%

Cp2TiC1 2 , N a ( H g )

I

Nugent, W.A,

1)

(4

* ; Calabrese,

Benkeser, R . A .

J.C.

J Am Chem ----

Soc,

(1984),

106,6422

80%

1 . C a ( s a n d ) , LBuOH

.

2. EDA, fiBuNH2

T H F , 24h

* ; Laugal,

90%

J.A.: Rappa, A.

Tetrahedron L e t t , ( 1984),

25, 2089


SECTION 377

*e+? "'gH1 3

1 . MeCH=CHCH2A1 i B u 2

C1 2 Z r C p 2 , D C E

nC 6H 3 C ~ C H -

2 . H30t Miller, J . A . ;

Negishi, E.

PhCH=CHCH20Ac

(r)

-

-\

60°C

25)

(75

*

-


1 . 5% P d ( P P h 3 ) 4 , RT P P h 3 , NaBr, THF MeOH 2 . EBuLi 3. PhCHO -1 7'C-RT

60%

25, 5863

PhCH=CHCH2CH=CHPh 82%

(EZ:EE

*

= 79:21)

Tsukahara, Y.; K i n o s h i t a , H. ; Inomata, K . ; Kotake, H. --Bull Chem Soc (1984), 57, 3013

EtOCH2C=CCH20Et

LiA1H4,

s,

MgBr2

E t 2 0 , 35°C

Barbot, F.; Dauphin, R.; Miginiac,

* P.

t

57%


0 I1

1 . Py, (EtO)*PCl O ' C , 2h

CH2=C=CHCH20Et

24 nB u

>

-

nBu 2 . CBuMgBr, CuI T H F , 0°C - R T 69% 12h Araki, S . : Ohmura, M.; Butsugan, Y. Synthesis, (19851, 963

H OCH C E C C H OH

SECTION 377

OLEFIN

* E . J . ; Desai, 0 II SMe 1

489

OLEFIN

1 . Ph3P=CHCH P h C H 3 , 23°C

Me CHO

Corey,

-

2. m c p b a , C H C 1 3 3. 50°C, 4h

65%

Tetrahedron E,(1985), 26, 5747

M.C. 0

I1

1 . CF3C)20,, C H 2 C 1 2 RT,

3h

2 . CH2=CHnC5H1 1 ,

ooc *

CH2=CHCH=CHnC5H1

C F 3 C O O H , 90 m i n 63% 3. m c p b a , C H 2 C 1 2 4 . 140°C I s h i b a s h i , H.*; Komatsu, H.; Maruyama, K.: Ikeda, M. Tetrahedron E,(19851, 26, 5791 CI

1. t B u L i , LBuOK

pentane/ hexane

2.

2 "C12H25Br THF,

Cordon 111, B.

Br

Engman,

lh

74% Mera, A.E.; Kumpf, R.J. --J Org Chem, (19851, 50, 1540

* : Blumenthal,

M.;

1 . N a B H 4 , MeOH 10%

Br

RT,

*

O - T e T e a

S

S

2 . HOH

* L. ; Bystrtim,

S.L.

93%

J Org Chem, (1985),

50, 3170

490 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 6 1.

4

~-Bu

fl

P h'

BrCH=CHPh,

PhH

Pd(PPh,), r e f 1 ux

B/OQ '0'

Miyaura, N.:

-

t

-

2h

86%

*

Yamada, K . ; S u g i n m e , H.; Suzuki, A. ---J Am Chem Soc, (19851, 107, 972

P h C H = C H 2 , PhH -

RuCl 2 ( P P h 3 ) 3 1 5OoC

*

-Chem L e t t ,

Kamigata, N . ; Ozaki, J . ; Kobayashi, M.

1. nBu2CuLi

H C E CH

Taylor, R.J.K.

.

* : Burford,

n-Bu

71 % S.C.


CuBr . S M e 2 , M e M g B r M e 2 S , Et20, - 4 5 ° C

n C 6 H 13CrCH 2 . C H 2 = C H C H 2 B r [Me2N],P=0, -30°C 3 . a q . NH4C1 I y e r , R.S. ; H e l q u i s t , P .

*

(19851, 705

w -

*

2 . Me1

1

-

-

* * B u s h

2 . NaOEt, E t O H ,

7

Furber, M.;

SECTION 377

E-

"'gH13

3rg Syn, (19851,

26,

3285

L/ 85%

64,1

SECTION 377

OLEFIN

-

die-/

1 . LiA1H4, 0°C - R T T, H 1F 8 h

*

2 . a q . NH4C1

3

Wang, K.K.

*

Epling, G.A.

491

OLEFIN

0°C ; Nikam, S.S.; Marcano, M.M.

WT3

--LJ

(E:I

= 4:l)

80%

6

-

Tetrahedron L e t t , (1986), 27, 1123 CN

@

, h v

CN

NaBH4, MeCN, H O H

* ; Florio,

*

H' Me

8h


E.

27,

86% 1469

PhCHO, dioxane P h C H = C H C H 20H

Pd ( a c a c )

,

r e f 1 ux

PhCH=CHCH=CHPh

lllh 53% * Moreno-Makas, M. ; OrtGo, R.M.; Prat, M . ; Gal&, M.A. Syn Cornnun, (19861, 1003 --

16,

Tsuji,

* J . ; Sugiura,

66% T.; Yuhara, M.; Minami, I. JCS Chem Comn, (19861, 922

---


e-,

PhCH=CHCH2C1

nBu3SnC1,

5OoC

DMF

PdC12, P P h 3 , Et4NOTs,

SECTION 377

*

P

h

G

P

h

24h

Yoshida, J . ; Funahashi, H.; Iwasaki, H . ; Kawabata, Tetrahedron Lett, (1986),

* N.

92%

3, 4469

Reviews: V a t a l y s i s of t h e Cope and C l a i s e n RearrangementsTr Lutz, R.P.

* -Chem Rev,

(1984),

84,

205

IIMercury ( 1 I ) a n d Palladium (11) Catalyzed [ 3 , 3 ] - S i p a t r o p i c Rearrangement Overrnan, L.E.

*

Angew Chem I n t ----

Ed=,

(19841,

23, 579

lrAsymmetric Diels-Alder and Ene Reactions i n Organic Synthesis"

O p p l z e r , W.

*

Angew Chem Int Ed

---

x, (1984), 23, 876

IIAcetylene Equivalents i n Cycloaddition Reactions" DeLucchi, O . , Modena, G. I1IT 3-


Allylpalladium Compoundsf1

J o l l y , P.W.

*

Angew --Chem I n t Ed

40,

2585

x, (19851, 24, 283


AUTHOR INDEX Abbott, D.E.: 187 A h , K.: 129 A b e , N.: 141 Abecassis, J.: 484 Abeywickreq, A.N.: 202 Abidi, S.L. : 007 Abiko, A.: 010 Abla, M.A.: 399 Abou-hsali ,*M. : 166 Abrams, S.R. : 008 Achiwa, K.: 276, 362, 377 Acker, M.: 232 Ackroyd, J. : 473 Adak, M.W.: 055 Adam, W. : 328 Adamczyk, M. : 292, 31 0 Adams, B.!: 468 Adams, C. : 038 Addess, K.J.: 331 Adkins, R.L.: 165 Adlington, A.M.: 097, 234 352, 424 Aebi, J.D.: 296 Aerssens, M.H.P.J.: 290 Agawa, T.: 107, 157, 188, 215 221, 289, 418, 465 Ager, D.J. : 059, 271, 355 Agosta, W.C.: 41 1 Aguero, A.: 225, 444 Ahlbrecht, H. : 121, 369, 369 389, 406, 464 Ahmed-Schof i e l d , R : 390 Ahn, K.H.: 200 Aida, T.: 140 Aihara, K. : $66 Aitken, R.A. : 003, 479 Aizpurua, J.M.: 185, 187, 240 Akase, F.: 2g2 Akermark, B. : 158 AkgUn, E.: 356 Akiba, E.i 271 , 327 Akiba, K. : 286, 345, 369 Akita, M.: 232 Akiyama, T.: 431 Akutagawa, S. : 389 Alajarin, M.: 034, 149

*

.

A l b i m t i , K.F.i 369 Albright, : 340 Alexakis, A. : 073, 089, 173 220, 389, 454, 486 Alexander, R.: 175 Allwood, B.L.: 037 116 Almnd, M.R.: Alneri, E.: 176 Alpegiani& M . : 018, 185 Alper, H. : 081, 082, 104, 139 145, 153, 155, 156 162, 163, 195, 196 200, 226, 231, 280 Altnau, G.: 086 Aly, M.F.: 362 Amari, E.: 477 Ambler, P.W.: 293 Amita, F.: 383 AmmanamancQi, R.: 128 Amos, R.A. :,140, 179 Amouroux, R. : 426 Anciaux, A4J.: 093 Anders, E. : 215, 458 Anderson, K.W.: 188 Anderson, O.P.: 310, 365 Ando, K . i 246 Ando, M. : 044, 253, 433 453, 458 Ando, R.: 092, 095 Ando, S.: 416 Ando, T.4 189, 221, 287 Ando, W. : 332 Andreoli, P.: 109 Andrews, S.W.: 322 Andrianome, M. : 069 Angle, S.8.: 412, 420 Anker, D. : 166 Annunziata, R.: 310, 311 Antebi, S.: 145, 163, 196 Antonini, I.: 365 Antonsson, T.: 422 Anwar, S.: 307 Anwer, M.K.: 0i;l Anzeveno, P.B. : 401

J.1.

Aono, T.: 158 Aoyama, T.:

126

493

494

INDEX

AUTHORS

*

Appel, R. : 140, 353 Aquadro, R.E.: 019, 039 Arai, H. : 252, 309 Arai, I.: 096, 287 Araki, K.: 003 Araki, S.: 253, 488 Araki, T.4 196 Arase, A. : 139, 246, 289 Arcadi , A. : 348 Arcelli, A.: 022 Arhin, A , : 116 Amani, E.: 449 Arrhenius, P.: 173 Arrieta, A.: 240, 448 Arseni jevic, L.i 059 Arsenijevic, V. : 059 Arseniyadis , S. : 387 Arvanaghi, M.: 226, 435, 449 Arya, P.S.: 031 Aryal-KaloustiaQ, S. : 41 1 Arzoumanian, H. : 446 Asai, N.: 302 Asami, M.: 098, 141 Asano, S.: 105 Asensio, G.: 145, 457 Aslam, M.: 486 Aslanian, R.: 106 ASO, Y.: 135 Assercq, J.-M.: 173 Atherton, J.I.: 003 Atkins, R.K.: 317 Atkinson, 3.G.: 179 Atoh, A.: 391 Atsunori, M.: 031 AttenbacQ, H.-J. : 218 Au, A.T. : 215 Aubert, C.: 188 Auburn, P.R.: 423, 443 Avasthi, K.; 265 Awata, T.: 143 Axiotis, G.: 334 Ayaguchi, Y.: Ayorinde, F. 0.g481 86 Azadoni, H.N.: 060 Aznar, F.: 205, 390

BEbkvd.1, J.-E.

*:

125,106 415, 416

Baba, T. : 262 Babler, J.H. : 237 Baca, S.B.: 294 Bach, J.: 201 Bachand, C.: 123 Bachanova, k.A. : 276 Bache, M.D. :*421 Baciocchi,,E. : 394 Back, T.G. : 199 Bae, S.K.: 358 Bagheri , V. : 143, 206 Bailey, T.R.4 122 Bailey, W.F. : 074, 174, 396 Baillargeon, V.P.: 059, 060 Baizer, M.M.: 143, 401 Bajgrowicz, J.A.: 363, 376, 378 Baker, G.i 126 Baker, R. : 219 Balabane, M.: 125 Balasuhrmanign, T.R. : 408 Baldwin, J.C.,: 097 Baldwin, J.EZ : 234, 352, 424 Baleja, J.D. : 169 Balkovec, J.M.: 412 Ball, T.F.: 427 Ballistregi, F.P.: 463 Balme, G. : 185 Balogh, M.: 225 Balss, f . : 232 Ban, Y. : 107, 363 Banerjee, A . : 055 Banfi, S.: 430 Baraldi, P.G.: 483 Baralt, E.: 136 Baran, D.: 106 Barbaruah, M. : 154 Barber, Y.J.: 294 Barbot, F. : 488 Barcelo, G.: 136 Barco, A , : 475, 483 Barluenga, J . : 110, 145, 205 224, 251, 252 267, 370, 384 390, 448, 457 '

AUTHORS

INDEX

*

Barnette, W.E. : 400 Barrans Jr.: R.E.: 032 Barrette, E.P.: 209 Barrio, J.R. : 193 Barrish, J.C.: 308 Barry, C.N.i 166 Bartoli, G. : 228 Bartoli, J.F.:,177 Barton, D.H.R. : 029, 031, 115

123, 129, 167 181, 194, 196 234, 259, 385 386, 460 Barton, J.C.: 091 Bartroli, J.:,313 Bartsch, R.A. : 446 Barua, N.C.: 154, 252 Baruah, J.N.:*154, 385 Basavaiah, D. : 284, 288, 338 Basha, F.Z.: 116 Battioni, P.: 177 Batuah, J.N.: 047, 179 Baudin, J.-B.: 064 Baudoux, DI: 459 Baudry, D. : 256 Bauer, T.: $37 Bauld, N.L. : 094 Bay, E.:,119 Beak, P. : 132, 372 Beaudoin, S. : 265 Beaulieu, P.L.: 149, 231 Bechstein, U.: 244 Beck, A.K.: Becker, C.: Becker, P.N.: 375 Becker, R.: 036 * Beckwith, A.L.J. : 200. 202 Bedeschi, A.: 0 8, 185. Bednarski, #.: 60, 437 Beebe, T.R. : 1 5 Beers, S.: 2g4 Begue, J.-P. : 88 Behnke, M. : 087 Behrooz, H.: 03 Belanger, P.C.: 468 Beletskaya. 1.P : 001 , 156, 221

495

Bell, T.W.*: 231 Bellamy, F.D. : 133 Bellasoued, M.: 294 Bellesia, F.: Belletire, +J.LfS? 291 Bellus, D. : 154 Belmonte, F.G.: 249, 256 Benati, L.: 380 Bencini, E.: 156, 304 Benetti, S.: 4x1, 483 Benkeser, R.A. : 032, 249, 256

487

Bennetau, B.: 023, 041 Bennett, R.: 106 Beraldi, P.C.: 471 Bergbreiter, D.E. : 055, 125

*

183

Bereplan, R.C. : 375 Bernad, P.: 251, 252 Bernard, D.: 476 Bernard, M.: 264 Bernardinelli, C.: 372, 412 Bernheim, M.: 285 Berryhill, S.R.: 108

Bertolini, G.: 298 Bertounesqufi, E.: 294, 334 Bertz, S.H. : 032 Berube, D. : 384 B e s t m , H.J. : 222, 336 Bestre, R.D.: 148 Beswick, P.J.: 077, 216 Betschart, C.: 383 Bhmddl,

H.: 444

Bhat, K.S.: 166, 344 Bhat, N.C.: 002, 284, 288, 457 Bhatnagar, A.K.i 037 Bhatnagar, S.P. : 115, 120 Bhatt, M . V . : 033 Bhushan, V.: 144, 213 Bienz, S.: 109 Bigelli, C.: 218 Billedeau, R.: 364 Biller, S.A.:'16g. Billington, D.C. : 430 Billion, A.: 386 Billmers, J.M.: 333

496

AUTHORS

Bin Manas, A.R.: 061 Bischoff, J.J.: 174 Bisling, M.: 259 Blankenship, C.: 320 Blanton, J.R,: 183 Blechert, S. : 368 Bloch, R . i 480, 484 Block, E . : 486 Blodgett, J . K . : 116 Bloom, A.J.: 110, 278 Bloom, S.H.: 079, 262 B l u m , Y.:

082

Blumenkopf, T.A.: 324, 443 Blumenthal,, M.: 489 Boche, G. : 285 b d e n , E . P . : 418 * Boeckman Jr.: R.K. : 050 Boensmann, H.: 300 Bogardus, C.C.: 165 Bogavac, M . 4 059 Boger, D.L. : 094, 392, 395 Boivin, J.: 386 Boldrini, G.P.: 135, 319, 349 Bolesov, I.G,: 094 Bonadies, F. : 155 Bonavoglia, F.: 090 Bond, F.T.: 265 Bonde, S . E # : 073 Bonini, C. : 155 Borders, R . J . : 325 Borg, R.M.: 390 Borschberg, H . J . : 150 Borush, R.C.: 385 Bosch, E.: 421 BOSCO, M. : $28 Bosnich, B. : 423, 443 Bottaro, J.C,: 234, 352 Boudjouk, P. : 445 Boukouvalas, J.: 352 Bouquet, M.: 158 b u r d o n , F.: 145 Bourgasser, P.: 462 Boutin, R.H.: 116 Bovicelli, P . : 159 i3oyd, S.D.: 245 Boyer, B. : 026

INDM

Boyer, s.K.". 201 Brady, W.T.*I 431 Braga, A.L.: 005, 286 a r a i s h , T.F.: 050 Branca, S.J.: 416 Branchaud, B.P. : 137 Brand, M.: 1z8, 450 Brandsma, L. : 290 Brannfors, J.M.: 210 Braun, M. : 020, 332 Elremmer, M.L.: 371 Brena, F.K.: 408 IBridon, D. : 029 Brinkman, K.: 227 Brinkman, K.C.: 354, 441 B r i t t o n , T.C.: 295 Broadley, K.: 111 Brocksom, T.J,: 399 Brookhart, M. : 093 Brotherton, C.E.: 094 Brown Jr.: Q.B.: 177 Brown, C.A.,: 002 Brown, H.C. : 002, 016, 044 051, 062, 097 283, 284, 288 317, 319, 320 329, 344, 453 457, 470 Brown, J . D . : 217 Brown, L.: 143 Brown, S.L.: 016 Brownbridge, PI: 445 Brunelle, D . J . : 171 Brunet, J.J,: 011, 185, 249 Brunner, H. : 036 Brunner, R.K.: 150 B r u t t s , D.: g24 Bryson, T,A. : 325 Biichi, G. : $74 Bubnov, Y.N. : 347 Buchan, C.: 153, 156 Buchman, 0. : 292, 248 Buchwald, S . L . : 264, 268 Bugden, G.: 308 Buhro, W.E.: 095 Bumagin, N.A.: 001, 156, 221

INDEX

497

AUTHORS

Bumgardner, C.k.*: 355 Bunnelle, W.H, : 427 bunnett, J.F. : 225 Buntin, S.A.: 053 Burford, S.C.: 490 Burgess, K.: 270 Burk, R.M.: 131, 388 BUSS, A.D.: 257 Butlers, M.:,191 Butsugan, Y. : 253, 488 Bystrtjm, S..E.: 106, 415 Bystrtjrn, S.L.: 489 B y W , H . - S . : 061 Cabal, M..-P.: 390 Cabre, J . :,099 Cacchi, S. 202, 348 Cahiez, G.*I 208, 220, 454 Caillaux, B.i 368 Cainelli, G. : 028, 109, 135 183, 463 Calabrese, J .C : 487 Callen, G.R.: 342 Calzada, J.G.: 006 Campbell, J . A . : 401 Camps, P . J . : 145, 457 Canella, K.A.: 021 Capdevielhe, P.: 195, 208, 466 Caple, R. : 478, Caporusso, B.M. : 263 Capozzi, G. : 002 Cardellicchio, C. : 089, 209 Cardellini, t$.: 365 Cardillo, G. : 314, 332 Carini, D . J . : 2i4 Carless, H . A . J . : 429 Carling, R.W.: 421 Carlon, M. : 224, Carlsen, P . H . J . : 052 Carrnan, L.: 353 Caro, B. : 026 Caron, M.: 316, 329 Carpino, P . A . : 374 Carpita, A.: 001, 281 Carr, S . A . : 347 Carre, M.C,: 462 Carrie, R. : 130, 133

-

.

Cartaya-Marin, C.P.: 223 Casares, A q . : 087 Casey, C.P. : 180 Casnati, G. :,449, 485 Castaldi, G. : 015, 451 Castaneda, A.: 443 Castedo, L.: 368, Castelhano, A . L . : 364 Castellino, S.: 404 Castro, B.: 017 Castro, J.L.: 368 Catellani, M.: 477 Caton, M.P.k.: 424 Caubere, P. : 011, 082, 185 * 249, 462 Cava, M.P. : 397, 481 Cavicchioli, S.: 451 Cefelin, P. : 260 Celebuski, J.E.: 392 eervinka,+O : 037 Cha, J.S. :,051, 179 Chabaud, B. : 172 Chakraborti, A.K.: 010, 148 Chakraborty, T.K.: 144, 161 Chalais, S.: 078, 226 Chamberlin, A.R. : 079, 262, 265 Chamchaang, W.: 257 Champney, B. : 165 Chan, D.M.T.: 412 Chan, T.H. : 140, 314, 404 Chan, W.K.: 150 Chandran, R.: 055 Chandrasekaran, S. : 135, 144 160, 161, 213, 238 Chang, H . : 136, 321 Chang, H.S.: 104 Chang, Y.K.: 358 Chanson, E.: 460 Chantarasiri, N.:+257 Chaona, S.: 257 Chapman, D. : 087 Chapman, K.T.: 307 Chapuis, C.4 372, 412, 413 Charles, G. : 118, 137 Chastanet, J. : 1 1 8 Chatani, N. : 058, 483

.

,

498

AUTHORS

Chatterjee, S.: 206, 441 Chattopadhyay, S. : 178 Chatzilosifidis, I.: 227 Chaudhuri, NIC.: 339 Chawla, H.M. : 274 Cheik-Rouhou, F.: 350 Cheikh, R.B.: 392 Chen, B.: 125 Chen, C.: 040, 055, 423 Chen, C.-S;: 042 Chen, M.-HI: 306, 456 Chen, Q-Y. : 001 Chen, S.-F.: 392 Chen, Y.-S.: 470, 475 Chenard, B.L. : 008 Cheng, Y.-S.: 371 Chianelli, 3.: 171 Chiba, K.:,107 Chiche, L. : 376 Chihara, T.: 3QO Chikashita, H. : 065, 084, 086 Chimichi, S.: 336 Chiusoli, G.P.: 477 Cho, B.T.: 319 Choabouni, R.: 392 Choi, V.M.FI: 435 Chong, J.M. : 002, 250, 293 297

Chou, C.S.: 053 Chou, T. : g79 Chou, T.-S. : 106 Choudary, B.M. : 054, 210 Chow, M.-S.: 287 Chowdhury, P.K.: 047, 179 Choy, W.: 350 Christol, H.: 056, 172 Christy, M.R.: 310 Chu, M.: 117, 371 Chua, V.: 032 Chung, B.C.: 104, 176 Ciaccio, J.A.: 331 Ciattini, P.Q.: 202 Cinquini, M. * 310, 311 Citterio, A.*: 090, 313 Claesson, A.*i 077 Clarembeau, M.: 068, 166

INDEX

Claremon, DIA.*: 380 Clark, G.R. : 476 Clary, D.W,: 273 Claudi, F. i 365 Claus, P.K. : 351 Clausen, K.: 102 Clawson, L.: 264 Clift, S.M.: i 5 4 , 437 Clive, D . L . J I : 149, 231 Coates, R.M. : 352 Coelho, F.: 291 Cohen, M.J.: 403 Cohen, T. : 432 Cole, E.R.: 148 Cole, T.E.: 002 Collington, #.W.: 049 C ~ l l ~ mD.B. , : 151, 265, 309 Colombo, L . : 298, 310 Colon, C. : 126 Colonna, S. i 430 Colvin, E.W. : 100 Comasseto, J . V . : 005, 286 Cominelli, A#: 090 Comins, D.L. : 028, 217 Concellon, J.M.: 251, 252, 267 Concepcion, J. I. : 182 Conley, R:A.: 393 Contento, M.: 109, 183 Contreras, R . : $21 Cooke Jr.: M.P. : 042, 087 Coombs, W.: 030 Cooper, A . J . L . : 304 Cooper, M.S,: 134 Corey, E . J . : 048, 091, 152, 169 209-, 235, 393 394, 438, 489 Cormons, A. :,373 Cornelis, A. : 078, 225, 226

-

273

Correa, I . D . : 429 Corriveau, J.: 172 Cortes, D.A.: 053 Cossec, B.: 376 Cossio, F.P.: 054, 209 Cottrell, D.A.: 101 Courtois, G I : 381

INDEX

Cousse, H,:

499

AUTHORS

426

D.P. : 190 Comes, B.: 487 cozzi, F.: 310, 311 Crabtree, R.H. : 082 Cramer, C,J.: 162 Crank, C. : 1 4 i Crawford, R . J . : 301 Crews, A.Q.: 126 Crich, D. : 181, 194, 196 Crisp, C.T.: 2Q2 Cristau, H.-J. : 056, 172, 376 Croft, A.P.: 446 Cronin, P.L.E.: 116 COX,

Cruz, A. : 408 Cuella, L.r 121 Cuervo, H. : 384

Cullin,,D.: 224 Cum, C. : 006 Cumins, C.H.: 352 Curci, R.: 463 Curran, D.P.=: 306, 333, 429 456

C z a r k i e , D. : 082D'sa, A.: 326 D'Angelo, Jc : 059 D'Incan, E. : 026, 222, 269 D'Onofrio, F.: 252 Da Settimo, F.: 263

Dabbagh, G.: 032 Dahan, N.: 049 Dalcanale, E. : 010 Dalpozzo, R.: 2$8 Danheiser, R.L. : 019, 034, 284 306, 373 432 Danishefsky, S. : 101, 360, 430

Daniewski, W.M.i

437 Dankwardt, J.W.: 027 Danson, L.: 024 Dao, T.V.: 019, 039 Dappen, M.S.: 162,

Darensbourg, M.Y. : 040 DasGupta, 8 . : 359 Daub, C.W. 424, 466 Dauben, W;G:*: 087

.

Dauphin, B.: 488 Dave, P.: 061 Daves Jr.: G.D.*: 168 Davidson, A.g.: 030 Davies, F.A.,: 114 Davies, S.C. : 016, 11 1, 163 170, 171, 227 It

262, 293, 306

Davis, A.P.,: 307 Davis, F.A. : 178, 333, 335 Davis, H.B.: 210 Davis, M.W.: 082 Davis, W.A.: 481 Dawe, R.D.: 329 De l a Pradilla, R.F.: 399 De Buyck, L . i 381 De Kimpe, N. : 130, 381 De Lornbaert, S.: 148 De Maldonado, V.C.: 257 De Poorter, B.: 177 De Souza Barbza, J.C. 089 De Vega, M.J.P.: 149 De VOS, M.J.: 022, 095 Deardorff, D.R. : 326 Degani, I.: 171 Degl'Innocenti, A. : 336 Delaney, N.g.: 471 Deleris, C. : 269 Dell'aira, D.: 394 Dellaria, J.F.: 295

,

Delrnas, M. i 253, 350

Delrnond, B. : 069 Delorme, D. : 046, 265 Delpeuch, J.-J.: 133 Dernailly, G.: 174 Demonceau, 8 . : 093 Denis, J.M. : 123 Denis, J.N.: 182, 193, 258 Denmark, S.E. : 162, 470 Depres, J.-P.: 291 Dequeil-Castain6, M. : 040 Des Abbayes, H. : 013, 221 Desai, M.C.: 002, 489 Desai, R.C.: 151 Deschamps, P. : 01 2 Deschenaux, R.: 085

500

Demotes, G . : 020 Deshayes, H.: 198

Deshmukh, M.N.: 276 Desmond Jr. : R.W. : 422 Desmnd, R . : 087 Despeyroux, B.: DeBernardis, J.F!'g 116 DeLuca, O.D.: 019, 039 DeLucca, G. : 187 DeLucchi, 0.: 492

DeRenzi, A.4 343

DeShong, P. : 1 6 1 , 378 Diab, J.: 166 Dickerhof, K.: 003 D i e t e r , J . W . i 4114 Dieter, R.K. : 174, 414 D i e t z , M.: 369, 406 Dilworth, B . M . : 429 D i t r i c h , K.: 334 D i t r i c h , L.: 033 D i x i t , V.: 281 Dixon, B.R.: 392 DiFabio, R.: 155 DiFuria, F.: 2z6 Djahanbini, Q. : 487 D j u r i i , S.W. : 105 DBtz, K.H.: 271 Doi, J.T.: 180 Dolan, S.C.: 196 Dolence, E.K.: 310 Dollinger, H.: 121, 389 Dornek, J . M . : 096 Donnelly, K.D.: 446 Dordor-Hedgecock, I . M . : 293 Dordor, I . M . : 293 Doria, G . : 082 Doritheau, A. : 476 Dorow, R.L.: 095, 295 Dorsch, D.: 150 Dossena, A. : 449 DOW, R.L.: 143, 313 Doyle, D.L.4 230 Doyle, M . P . : Q95, 143 Dreiding, A.S. : 473 Dresely , S . :,348 Drewes, S.E. : 417 Drozda, S.E.: 075

AUTHORS

Dua, 5 . K . :

INDEX

031 072 Dubois, J.-E. : 294, 334 Dudf i e l d , P. : 089 DuSlos , A. : 426 Dufresne, C.: 068 Dufresne, Y,: 046 Duhamel, P. : 351, 459 Dumont, W.: 193 Dunach, E.: 276, 277 Duncan, M . P . : 335 Dunlap, N . K . : 405 Dunn, B.S.: 346 Dunogues, J. : 023, 041, 269 Dupuis, D . : 372, 413 Dupuy, C . : 089 Duraisamy, M. :,238 Duthaler, R.O. : 403 Dzhemilev, U.M.: 034, 083 Eapen, K.C.: 074 Eberlein, T.H.: 444 Edstrom, E.D.: 178 Edwards, P.D.: 122 Ehrenkauf'er, R.E. : 135, 378 Eickhoff, D.J,: 467 E i l b r a c h t , P. : 232 Einhorn, J.: 060, 107 E i s , M . J . : 430, 123 Eisch, J.J. : 031, 264 E l Gharbi, R.: 350 E l Hallaouri, A.: 363, 378 El-Abed, D.: 303 El-Telbany, F.: 027 Eliasson, K.M.: 014 E l l i o t t , J.: $58 E l l i o t t , J . D . : 031, 282, 292 435 E l l i o t t , R . : 282 E l l i o t t , R.L.: 306 Elofson, R.M.: 124 Elsevier, C.J.: $49 Elshaf'ie, S.M.M. : 149 Emblidge, R.W.: 14G Ehda, J . : $82 Enders, g. : 353, 402 Endo, T. : 196, 248

Dua, S.S.:

INDEX

501

AUTHORS

Engel, N.i 300 Engel, R. : Engler , T. 4. 424 Engman, L. : 271, 489 EYholm, E.J.: 390 Enner, B.: 254 Ehterzari-Moghadgam, M. : 21 4 Ephritikhine, M. : 256 Epling, G,A. : 491 Erdik, E. : 097 Erickson, W.F.: 083 Ermolenko, M.S.: 218 Ernst, A.B.: 410, 419

Fernandez-Simon, J.L. : 267 Fernandez, H.: 121 Ferraboschi , P. : 060 Ferrera, L. : 370 Ferroud, D.: 319 Ferroz, H.MIC. : 399 Fetizon, M. : 049 Fiandanese, V. : 089, 206, 209 Fiaschi , R. : 447 Fieehter, A,: 318 Fiegenbaun, P.: 254 Field, L.D.: 192, 246 F i e l d s , K.1.: 152 Ertas, M.: 335 Fife, W.K. : 385 Escoula, B.: 189 F i l i p p i n i , L.: 312 Eswarakrishnan, V. : 486 F i l i p p o Jr.: J.S. : 146 Etinger, M.Yu.: 347 F i l l e r , R.: 452 Eto, H.: 412 F i n e t , J.-P.: 167 EtteP, J.B.: 04.j F i n k , D.M.: 306 Evans Jr.: S.A. : 166, 167 Finkler,,S.H.: 218 Evans, D.A. : 081, 295, 307, 313 Finn, J. : 333 Evstigneeva, R.P.: 052 Finn, M.C.: $25 Fiorenza, M. : 229, 313, Ewing, J.C.: 346 .. 315 Exon, C.M.: 325 236 Firouzabadi, H. : 053, 054, 056 Eyman, D.P.: 051 Fabryova, A,: 037 211, 213, 214 Fadel, A, : 253 Fischer, H. : 170 Failla, S. :,463 Fischetti, W.: 387, 486 FdLCk, J.R. : 185, 349, 439 Fishel, D.k.: 014 Falmagne, J.-B.: 297 Fitjer, L. : 266 Falter, W.: 424 F i t z , T.: 330 Fankhauser, J.E.: 295, 372, 374 Fitzner, J.N.: 295, 363, 372 Farooq, 0.: 244 374 Fauvarque, S.-F.: 013, 260 Fleischmann, M. : 110 Fazio, M.J. : Fleming, I. : 045, 070, 092 Feigenbaum, A. 'P2459 258, 402, 438 Fekarurhobo, C.K.: 429 Fleming, J,A.: 267 Fekih, A,: 031, 123, 259 Flinch, H; : 049 Felkin, H.: 256 F l i p p i n , L.A.: 319 Felman, S.W.: 437 Flood, L.A.: 043, 158 Fengl, R.W.: 163 Flores, H. J. : 408 Fenk, C . J . : 333 Florez, J.: 224 Ferguson, G.S.: 346 Florio, E.: 491 Fergusson, S.8.: 155 Flynn, D.L.: 295 Feringa, B.L. : 355 Foa, M.: 013, 156, 304 Fernuldes, J.B.: 068 Fobare, W.F., 317, 384, 388

?'

*

~

*

~

502

INDEX

AUTHORS

Fochi, R.: 171 Foglio, M.: 018 Fomani, M.: 451 Forcellese, M.L. : 159 Ford, W . J . : 264 F o r t , Y.: 082 Fortgens, H.P.: 373 F o r t i n , R.: 048, 165 Foucaud, A. : 096 Fournet, C. :,185 Fowler, F.W. : 117, 317, 371 Francalanci, F.: 013, 156, 304 Francisco, C.G.: 182 Frank, R.K.: 361 F r a z i e r , J.: 317 Freerksen, R.W.: 231 F r e i r e , RI: 182 Frejd, T. : F r e n e t t e , R . f 7 I 65, 382 Freudenberger, J.H.: 255 F r i e d r i c h , E.C. : 096, 187 F r i o u r , G.: 248, 220 F r i s t a d , W.E. : 067, 161, 162 195, 393, 410

419, 446

Fry, M.A.: 195 Fuchigami, J . : 143 Fuchs, P.L. : 050 Fuentes, L.M.: 119 Fugami, K.: 263 F u j i i , K.: 014, 219 F u j i i , S.: 058, 484 Fujimoto, K. 029 Fujimoto, Y.i: 428 Fujinami, T.: 153, 160, 473 Fujisaka, S.: 015 F u j i s a k i , S.: 116, 144, 172

*

366

Fujisawa, T. : 008, 020, 051 068, 184, 207 234, 250, 341 416, 425 F u j i t a , E . i 359 F u j i t a , E. : 212, 267, 357 F u j i t a , M.: 311, 315, 351 F u j i t a , Y.: 360, 482

Fujiwara, I.: 172 Fujiwara, J.: 038, 122, 485 Fujiwara, T.i 246, 327, 433 Fujiwara, Y. : 070, 342 Fujiyama, R.: 452 Fukagawa, T. : 342 Fuks, R. : 259 Fukuda, Y. : 283 Fukui, M.: O!#3 Fukmoto, K. : 103, 119 Fukutani, Y.i 096 Fukuyama, T. : 049, 361 Fukuzaki, K . i 465 Fukuzawa, S. : 153, 160, 260

*

447, 473

Funabiki, T. ,239, 243 Funahashi, H.: 492 Funakoshi , K. : 460 Funakoshi, Y.: 242 Fung, A.P.: 108, 192, 246 Furber, M.: 490 Furukawa, H. : 438 Furukawa, Y. : 400 Furuta, K.: 170, 283 Fustero, S.: 384 Gadallah, F.F.: 124 Cadras, A , : 269 Gagnier, R . f l . : 074 Gais, H.-J. : 142 Galamb, V. : 280

Galan, M.A.: 191 Gallagher, T. : 379 G a l l i , C . i 225 Gallo, R. : 006, 012 Gallos, J.: 156 Gamboni, R.: 323 Ganboa, I,: 448 Ganem, B. : 030, 123, 134, 259 Ganguly, A. : 440 Ganushchak, N.I.: 400 Garcia F r a i l e , A.: !#56 Garcia Martinez, A. : 080, 456 Garcia, J.: 099 Card, G.L.: 210 Gardano, A.: 013, 156, 304 Gardrat, C.: 225

INDM

G a r i g i p a t i , R.S.: 381 Garland, R.4 404 Garst, M.E. : 173

Gartiser, T.: 133 Gasc, M.B.: 132 Gaset, A.: 2534 350 Gasparrini, FI : 237, 275, 276 Gassmn, P.G. : 316, 330 Gassner, T.: 215, 458 Gaudino, JI: 405

Gaus, P.L.

503

AUTHORS

-

: 020

Gauthier, J.Y. 030, 145 Gebreyes, K.: 4 i 6 Gee, S.K.: 019

G e l l e m n , B.J.: 446 Genet, J.P. * 125, 379 Gennari, C.": 298, 310, 411

George, J.: 135 Georgiodis, G.M.: 041 Gerdes, J.M4: 087 Gerlach, H. : 015 Germon, C.: 389 Gerstmns, A.: 078 Gervais, C.: 166 Ghadiri, M.Ri: 083, 290 Ghatak, U.R. : 010, 148, 359 Ghelfi, F.: 452 Ghirlando,,R. : 383 Ghosez, L. : 101, 148 Ghribi, A.: Giacanelli, 282 Giacomini, D. : 109 Giang, Y.F.: 431 G i a n g i o r d p o , M.A. : 1 1 4 Giese, B. : 016, 057, 097, 160 Giesema#n, G. : 105 G i l , G. : 354 G i l , J.B.: 152 G i l b e r t , J . C . : 357 Gilbert, L.: 480 Gilbertson, S.R.: 321, 442 G i l l a r d , J.W.: 048 G i l l e s p i e , D.G.: 005 Gilman, J.W.: 410 Ginos , J. Z :,304 Giordaro, C. : 015, 451

A?:

.

Giovannini, F.: 318 Giovannoli, M.: 237, 275, 276 Givre, S.: 374 Gladysz, J . A . : 354, 441 Glens, Y.-F.: 392 Glue, S.E.J.: 236 Gnevasheva, L.M.: 432 Codel, T.: 089, Godleski, S.A. : 437 Godoy, J.: 052, 275 Godschdlx, J.P.: 472 Goering, H.L. : 070 Goh, S.H.: 200 Golebiowski, A.: 437 Gonzalez-Nunez, C : 1 45 Gonzalez, A.: 054, 209, 462 Gonzalez, J.M.: 457 Gopal, M.: 200, 280 Cora, J.: 057 Cordeev, K.Yu.i 052 Gordon 111, : 489 Gordon, E.M. : 471 Gordon, H.J.: 382 Gore, J.: 185, 387, 487 Gore, M.D.: 364 Goto, K.: 337 Goto, T.: 240 Gotoh, Y.: 341 Cotor, V.: 384 Could, T.J.: 294 Govindan, S.V. : 093 Gowriswari, V.V.L. : 338 Graff, M.: 420, Gramain, J.-C. : 363 Gramatica, P.: 233 Grandi , R.4 452 Gravel, D. : 065, 238 Greck, C.: 1 2 4 Greene, A.E. :,291 Greenlee, W.J. : 296 Greenspoon, N. : 086 Grehn, L.: 138 Grey, R.A.: Gribble, G.WZ'7 021, 241, 327 Grieco, P.A. : 295, 317, 384

.

8.

388

504

Grierson, D.S.: 133 Griesbeck, A.: 328 Grift%, 3.H.: 095, 260 Grigg, R. : 061, 362 Grigor'eva, #.Ya. : 197 Grimaldi, J. : 373 Grim, E.L.: 152 Gringore, O.H.: 299 Gross, A.W.: 394, 438 Grote, J.: 427 Groult, A,: 314 Groves, J.T.,: 177 Grubbs, R.H. : 207, 264, 268 Gruber, J.M.: 392 Grundkq, G.: 450 Giiell, F.; 462 Gu, X.-P.: 434 Guedin-Vuong, D. : 287 Guerrier, L. : 133 Guette, J.P.: 158 Guggenheim, T.L. : 137 Guillemin, J.C.: 123 Guinamant, J.L.: 401 Guindon, Y. : 029, 046, 048 049, 165, 179 Guixer, J.: 430 Gulevich, Yu.V.: 156 Gull, R.: 377 Gunnarsson, K.: 138 Guo, M.: 413 Gupta, A.K.: 317 Gupta, B.G.BZ: 189, 191 Gupton, J.T. : 106, 126 Gurmni, F.: 015 Guseva, S.A.: 016 G u t t i e r i , M.J.: 198 Guy, A.: 158, 314 Gybin, A.S.: 478 Gyoung, Y.S.: 022 Hzssig, 4.: 439 Haas, A. : 186 Haberman, L.M.: 316 Hackett, S.: 147 Hafeli, 1.K.: 037 Haga, K. : 124 Hagenak, J.A.: 301

AUTHC&S

INDEX

Hagihara, T.: 261 , 478 Hagiwara, I. : 228, 467 H a h n , C.S.: 338, 358 H a h n , G.: 22$, 282, 323, 339 Haines, S.R. : 170, 428 Hajipoor, Q.: 053 H ~ U , S.S. :*131 Hallberg, A. : 263 Hallock, J.S.: 151 Hamachi, I#: 34.1 Hamada, T. : 014 Hamada, Y.: 107, 157, 482 H m t o , I.: 269, 270, 349 412, 475 Hamamto, J . : 180 Hamana, H. 024, 335 Hamarfa, M.*(I 235 H m t a n i , T.: 013, 285, 342 Hamel, N.: 153, 156 Hamel, P.: 382 Hammond, G.B.: 224 Han, G.R.: 475 Hanaf'usa, T. : 189, 483 H a n w t o , T.: 305, 313 Hanazaki , Y. :,135 Hanessian, S. : 046, 265 Hanna, I.: 049 Hannon, F.J.: 091 Hansen, H.-J.: 169, 417 Hanson, R.M.: 325 Haque, M.S.: 004, 058, 152 335, 450 Hara, K.: 009 Hara, M.: 230 Hara, S.: 354, 455, 457 Harada, J.: 303 Harada, T.: 032, 093, 271 327, 341, 443 Harano, Y.: 107, 157 Harigaya, Y.: 396, 427 Harmata, M.A.: 470 Harnisch, HI: 016 Harpp, D.N. : 035, 140 Harre, M.: 404 Harris, F.L.: 418 Harrison, LW.: 415, 439

505

AUTHOpS

INDEX

Hart, D.J.*: 1 1 4 Hartmann, H. : 306 Hartner Jr.i F.W. : 437 Hartwig, W. : 197 HaruSawa, S. : 482 Haruta, J.: 159, 336 Haruta, R.: 283 Harvey, D.F.: 430 Haaegawa, M.: 339 Hasegawa, T.: 216 Hashimto, H.: 070, 201 Hashimto, K.: 212 Hashimto, S.: 376, 383 Hasimoto, H.: 255 Haaskerl, T.: 160 Hasson, D : 484 Hata, K.: 212 Hatanaka, Y. : 342, 479 Hatano, M.: 253 Hatayama, Y.: 170 Hauptmann, S. : 108 Havens, N.: 140 Hayama, T.: 297 Hayami, J.: 412 Hayashi, H.: 334 Hayashi, J. : 064, 237, 472 Hayashi, K. : 270, 338, 465 Hayashi, N. 456 Hayashi, T. : 023, 075, 261 299, 341, 341 Hazra, B.: 055 He, G.-X. ;,078 Heaney, H. : 134 Heasley, G.E. : 447 Heasley, V.L.: Heathcock, c . H . ? ~ ~ I324 ~, Hebel, D.:*191 Hebert, E.*: 234 Heck, R.F. : 453, 380, 387, 486 Hegedus, L.S. : 365, 454, 468 * 469 Heilmann, S.M. : 168 Heimbach, H.: 227, 404 Hellwig, G. :,216 Helmchen, G. : 088, 146, 150 306, 320

.

*

Helquist, P. : 227, 490 Hembre, R,T.: 155 Henin, F. : 374, 423 Hennequin, L.: 451 Henning, R.: 045 Henzen, A . V . : 436 Hernandez, D. : 258 Hernandez, R. : 182 Herndon, J.W.: 413, 463, 482 Herranz, E.: 312, 314 Herrera Fernandez, A . : 080 Herrick, J.J.: 028 Herrmann, R.: 2$2 Hershberger, J. : 088 Hershberger, S.: 088 Hershberger, S.S.: 073 Hertel, G.R.: 106 Herzig, JI: 440 Hesse, M. : 109, 158, 403 409, 458 Heuckeroth ,,R .O : 1 19 Hemann, A. : 158, 422 Heveling, J. : 081, 195 Heyn, A.S.: 083 Hibino, J . : 478 Hickmott, P.W. : 392 Hidai, M.: 2&2 Hiegel, G.A.,: 450 Hiemstra, H. : 102, 371, 373 Higashimura, H. : 394 High, J.: 224 Higuchi, K.: 207 Higuchi, N.: 309 Higuchi, T.: 075, 321 H i i , P.S.: 165 H i k i m a , H.: 318, 330 Hild, W.: 332 H i l l , C.L. 177, 178 H i l l , J . G . : 325 Himlsbach, R J. : 063 Hirakawa, g.: 327 Hirama, M. : 318, 366 Hirano, M.: 211 Hirao, A.: 036, 038 Hirao, I.:. 030, 285, 288, 393

.

.

.

506

AUTHORS

Hirao, T.*: 107, 157, 188, 215 221, 289, 418, 465 Hirashima,,T.: 057, 344 Hirobe, M. : 321

075 311, 315, 341 342, 405 Hiyoshi, T.: 135 Hodge, P. : OQ4, 183 Hoffman, R.V. : Q58 Hoffmann, H.M.R. * 055, 477 Hoffmann, H;M.g.*i 477 Hoffmann, R.W. : 024, 033, 334 * 348 Hojo, M. : 028, 065, 394, 398 Holman, N.J.: 170 Holmes-Smi th, R. : 256 Holmes, A.B. : 421 Holmes, 2.J.: 474 Holy, N. : 136 Holzapfel, W.: 218 Homoto, Y.: 032 Hong, C.Y.: 200 Hoole, R,F.A.: 417 HOOZ, J. : OOQ Hopkins, P.R. : 295, 363, 372 374 Hori, Y.: 290,,423 Horiuchi, C.A. : 302 Horler, H . : 057 Hormi, O.E.O.: 366 Horne, D.: 405 Horne, S.:,364 Horner, L. : 003 Hoshi, M. : 139, 246, 289 Hoshino , M. :,411 Hosokawa. T. : 355 Hosomi, A.: 044; 064, 237 377, 430, 443 453, 472 Hotchkiss, L.M.: 049 Hotta, Y.: 023 HOU, K.-C.: 333 Houpis, 1 . N . i 042 Howard, A.S. : 383 Hrubiec, R.T.: 126, 182, 261 Hirotsu, K.:

Hiyama,.T.*:

INDEX

HSU, M.H.: 415 HSU, S.-Y.: 470, 475 Htillmann, M.: 025, 041 Hiherbein, J. : 140 Hua, D.H.: 048 Huang, S.$B.: 206 Huang, Y. : 055, 359, 419, 425 Huang, Y.Z.: 040 Huber, I.: 101 Hubert-Habart, M.: 241 Hubert, A.J.: 093 Hubert, T.D.: 051 Hubner, F. : 227 Huckstep, M.Q.: 424 Hudlicky, T. : 093, 353 Hudrlik, A.M.; 441 Hudrlik,,P.F. : 441, 454 Huet, F. : 356 Huf'f, B.: 361, Huffman, J.W. : 042, 151, 461 Huggenberg, W.: 403 Hui, R.A.H.F.: 300, 431

Hui, R.C.:,397, 461 Hujama, T. : 425

Hulce, M. : 088 Hung, M.-H.:,413 Hunter, D.H. : 460 Husain, A . i 011, 047, 182 H u s k , G.R. : 093 Hussain, M. : 407 Hussein, F.H.i 2 2 Husson, H.-P. i 33 Hutchins, R.O. : 027 Hvidt, T. : 298 Hwang, C.K.: 184 Hwang, Y.S.: 117 HWU,

J.R.%:,032, 236

Hyatt, J.A. : 273 Hylarides, M.D.: 455 Hyuga, S.: 457 I b e , M.: 4Q4 I c h i h a r a , J. : 098, 141, 189 Ichikawa, M.: 076 Ichinose, H,: 022, 040 Idoux, J.P. : 106, 126 I g a r a s h i , T.: 219

AUTHORS

INDEX

Iguchi, K.: 071 Ihara, M.: 103, 119 Iida, H.: 009, 058, 351, 358 Iida, S.: 068, 184, 250 Iihama, T.: 358 Ikariya, T.: 144 Ikeda, H.: 467 Ikeda, I.: 434 Ikeda, K.: 276, 362, 377 Ikeda, M.: 078, 483, 489 Ikeda, N.: 254, 283, 284, 433 Ikeda, Y.: 254 Ikegami, S.: 297 Ikemi, Y.: 376 Ikemoto, Y.: 342 Imada, Y.: 373 Imai, H.: 356, 435 Imai, T.: 016, 062 Imai, Y.: 044, 099 Imaizumi, M:I 239 Imamoto, T. : 042, 183, 277, 326 331, 342, 348

Imanishi, T.: 337 Imwinkelried, R. : 045, 346, 375 Inaba, S.: 071, 206, 245, 340 Inaba, T.: 351 Inada, A.: 5139 Inamoto, T. * 084 Inanaga, J.": 147, 199, 251 331 9 344, 395

Inokuchi, T,: 237, 299, 440 Inoroata, K. : 138, 142, 488 dInoue, K.: 210, 338 Inoue, N.4 456 Inoue, S. : 105, 336 Inoue, T. : 028 Inoue, Y.: 070, 201, 255 Inouye, M.: 135, 190, 262, 421 Inui, Y.: 203 Ipasli, S.: 006 Iqbal, J.: 402 Iranpor, N. :,053, 056, 21 4 Ireland, R.E. : 305 Iritani, K.i 422 Isagawa,,K. : 044 Ishi, Y. : 311

507

Ishibashi, H.*: 078, 489 Ishida, N.: 033, 205 Ishida, Y.: 729 Ishiguro, M.: 244, 283 Ishiguro, S.: 022, 040 Ishiguro, Y.: 460 Ishihara, K.4 031, 287 Ishihara,,T. : 221, 287 Ishii, Y. : 039, 144, 211, 454 Ishikawa, M.: 310 Ishikura, M.: 127, 375, 388 Ishimto, g.: 065 Ishino, Y. : 344 Ishiyama, T.: 076 Isimura, A.: 219 Ismailov, M.I.: 432 Isobaev, M.D.: 432 Isobe, YI: 422 Isoe, S. : 4ft5, 472 Itabashi, K. : 009, 242 Ito, K.4 036, 038, 130 Ito, S. * 056, 075, 366, 466 Ito, Y.*I 299, 309, 312, 356 380, 435, 478

Itoh, F.4 397 Itoh, K. : 065, 084, 086 252, 308, 418

Itoh, Kao.: 240 Itoh, Kaz.: 240 Itoh, T.: 439 Itsuno, S. : 036, 038, 130 Ives, J.L.: 461 Iwahara, T. : 027 Iwaki, M.: 176 Iwakiri, H.4 432 Iwakuma, T. : 120 Iwasaki, F.: 338 Iwasaki, G.: 235 Iwasaki , H. : 492 Iwasawa, N.: 168 Iwashita,,M. : 31 8, 366 Iwata, C. : 337 Iwaya, K.: 124 Iyer, P.SI: 175, 490 Iyoda, :M: 076 Izawa, T.: 220

508

AUTHCIRS

Izawa, Y.: 248, 456

Izumi, A.: 022, 040 Izumi, T.: 028 Izumi, Y.: 165, 337, 444

475, 482 Jdger, E.4 351 J a b r i , N. : 486 Jacquesy, J.;C.: 315 J a c q u i e r , R. : 363, 376, 378 Jadhav, P.K.: 002, 320, 344 Jagdale, M. : 409 Jagdmann Jr.: E.: 201 Jagdmann Jr.: C.E.: 122 J a g u e l i n , S.: 401 Jain, A.U.: 352 Jakovac, I.J.: 146 James, .B.R. : 215 Jamil, Z.: 054, 210 Janes, J.M.: 447 Janout, V.: 260 Januszkiewicz, K.R. : 081, 082 231 Jaouen, C. : 026 Jasperse, C.P.: 301 Jaworski, K. :*442 J e f f o r d , C.W. : 352 Jellal, A. : 281 , 303 Jensen, K.M. : 168 J i , T.: 330 Jimenez, C.: 110 Jitsukawa, K. 027, 211 Johnson, A.P.i: 366 Johnson, A.T.i 173 Johnson, C.R. : 434 Johnson, R . A . i 325 Johnson, W.S. : 031, 282, 292

435

J o l i d o n , S.4 169 J o l l y , P.W. : 492 Jonczyk, A , : 435 Jones, D.S.4 137 Jones, J.B. : 146, 300 Jones, M.D.: 391 J o s h i , N.N.: 477 J o s h i , P.L.: 166 Jouannetaud, M.-P. : 31 5

Jousseame, B.: 460 Joussen, R.: 302 Juge , S. :,379 Julia, M.*: 064

INDEX

J u l i a , S. : 430 Jung, A.: $40 Jung, M.E. : 301 J w g , S.-H.: 374, 480 Jurczak, J.: 437 Jurss, C.D.: 126 Just, G.: 255 Jutand, A.: 013 Juve Jr.: H.D,: 392 Kabalka, C.W. : 132, 233, 235 432, 453, 455 Kabeta, K.: 261, 341 Kachinsky, J.L.C.: 479 Kadokura, M.: 001, 1 1 4 Kaesler, R.1.: 462 Kagan, H.B. : 024, 177, 220 276, 277, 307 Kageyama, I.*: 144, 21 1 , 448 Kagiya, T. : 120 Kagler, H.: 018 Kahne, D.E.: 084 Kai, Y.: 388 Kaiser, Q.A. : 452 Kaji, A. : 180, 269, 270, 349 4J2, 417, 422, 475 Kajigaeshi, S. : 015, 116, 144 172, 366 Kakihana, M.: 270 Kakimoto, M,:*38? Kakushima, M. i 382 Kallmerten, J . : 294 K m d a , M.: 127, 375, 388 Kamazawa, S. : 065 Kambe, N . : 454 Kaneda, T.: 138 Kamtani, T.: 103, 119 Kameyama, M . i 127, 192 Kamigata, N. : 192, 490 Kamimura, A.: 349, 417 Kamitori, Y.: 028, 065 Kanai, K.: 1 1 4 Kanatani, R.: 027

INDEX

AUTHORS

Kanbara, HI: 439 Kane, V.V. : 230 Kaneda, K . : 027, 211 Kaneko, R.: 124 Kaneko, Y.: 220, 384, 433 Kanemoto, S.: 214, 328, 357 Kang, G.J.: 314 Kang, J.: 256 Kang, M.: 393 Kano, T.: 273 Kantam, M.L.: 054, 210 Kao, L.: 280 Kao, S.C. : 040 Kapnang, H.: 118, 137 Karabelas, K . : 263 Karasawa, A . : 443 Karmarkar, S.N.: 241 Karpf, M.: 473 Kasahara, A.: 236 Kashimura, S.4 104, 217 Kashimura, T. : 156 Katajima, T.: 308 Katayama, E.: 038 Kates, S.A.: 407 Kathawala, F.G.: 217, 322 Kato, J.: 010, 168 Kato, S.: 131, 170, 426 Kato, T.: 438, 455 Katoh, A.: 448 Katoh, T.: 233 Katritzky, B.R.*: 034 Katsuki, T. : 288, 297, 305 312, 313 Katsuro, Y . : 261 Katz, A.H.: 247, 393 Katz, R.B.4 383 Kstz, T.J. : 019 * Katzenellenbogen, J.A. : 191 Kauffmann, TJI : 254, 259, 302 Kawabata, N. : 492 Kawada, K.: 331 , 451 Kawada, M.: 003, 009, 047, 461 Kauada, N. : 044 Kawaguchi, K.: 452 Kawahara, S.: 144 Kawaharasaki, N. : 099

509

Kawai, M. 1 155, 444 Kawai, T.: 2;50 Kawakami, Y. : 072 KawamOto, K . : 077 Kawamura, K.: 395 Kawamura, S.: 364, 367, 398

400, 428

Kawanami, Y.: 288 Kawanishi, Y.: 211 Kawasaki, M.: 315, 343 Kawashima, M. : 41 6 Kay, I.T.: 236 Kaye, P.T.: 452 Kayo, I.: 107

297 .

Kel y eC.E. Keck, ye: 390, 418 Keese, W.:,450 Keinan, E. : 004, 037, 08b

330 440

Kelkar, S.L.: 241 Kell, D.A.: 3x8 Kellogg, R.M. : 260, 323 Kelly, J.W.: 166, 167 Kelly, M.J.4 412 Kelly, T.R. : 130 Kelly, W.J.: 279, 406 Kemmitt, R.D.W.: 391 Kempf, D.J.: 372 Kesseler, KI: 332, 340 Kessler, H. : 017, 018 Kestner, V.M.: 406 Keumi, T. : 203 Kezuka, H.: 007 Khai, B.T.: 022 Khamsi, J.: 167 Khan, M.N.I.: 415 Khan, Md.NII.: 455 Khan, N.H. : 407 Kharitonova, O.V. : 141 Khoshdel, E.: 183 Khoudary, K.P.: 032 K ~ O U Z , B.:

420

Kiaeezadeh, F.: 056, 214 K i j i m a , M.:,248 Kikuchi, H. : 062 Kikuchi, T.: 266, 476

Kikukawa, K.

K i m , B.M.:

INDEX

AUTHQRS

51 0

* : 078

044, 322

Kim, C.-W.: 392, 475 D.: 456 J.-I.: 387 J.D.: 179 J.E.4 179 ~ . g . : 338, 358 S. : 099, 136, 140, 142 152, 200, 218, 321 K i m , S.-C.: 097 K i m , S.S.: 099 K i m , W.J.: 321 K i m , Y.C.4 140 K i m , Y.H. : 104, 176 K i m , Y.J.: 200 Kimura, K.: 341 Kimura, M.: 012 Kimura, T. : 065, 480 Kimura, Y.: 164, 340 King, A.O.4 006 King, F.D.,: 382 King, P.F. : 050, 138 King, S.A.: 42s Kinoshita, H. 138, 142, 488 Kiolle, R.: 379 Kircheyer, S.: 435 Kirihara, T.: 103 K i r k , T.C.4 223 Kirmse, W. : 216 Kirschleger, B.: 168 Kirshenbam, K.S.: 300 Kirszensztejn, P. : 164 Kirtane, J.G.: 175, 178 Kishi, N. : 340 Kishigamj,, Y.: 039 Kita, Y. : 336, 397 Kitagawa, Y.: 292 Kitahara, E.: 283 Kitajima, H.: 203 Kitamura, K . i 144 Kitching, WI : 074 Kiyooka, S. : 307, 324, 452 K jeldsen, G. :,468 Kjonaas, R.A. : 091, 226, 480 Klang, J.A.: 067, 195 Kim, Kim, Kim, Kim, Kim, Kim,

.

Klaver, W.J.: 102 Kleijn, H.: 438 Klingstedt, T.: 157 Klunder, J.M.: 329 Knapp, F.F.: 453 Knapp, S. : 367 Knoch, F.: 140, 353 Knochel, P.: 415 Knouzi, N.: 133 Knudsen, 3.S.: 468 Kejver, A.: 055 KO, J.S.: 200 KO, S.Y.: 328

KO, Y.K.:

142

Kobayashi , H. : 023, 103 Kobayashi, M. : 035, 072, 192 490 Kobayashi, S. : 433 , 462 Kobayashi, T.: 203, 243, 364 * 398, 409, 481 Kobayashi, Y. : 009 Kobori, Y.: 075 Koch, K.: 371 Kochetkov, N.K.*: 218 Kochhar, K.9.: 101 Kochi, J.K. : 176 Kodera, Y.: 124, 141 Koga, K.: 463 Kogure, K.: 062 Kohama, H. : 425 Kohmto,,S.: 352 Kohn, H. : 374 Kohno, S.: 188 Kojima, A&: 272 Kokel, B. :,241 Koketsu, J. : 079 Kokko, B.J.: 132 Kokosi, J.: 063 Kolbasenko, S.I.: 367 Kolhe, J.N.: 352 Kolodziejski, W. : 078 Kolosnitsin, V.S.: 276 Komada, S.: 434 KOmatsu, H.: 489 Komatsu, T. :,391 Kometani, T. : 330

INDEX

AUTHORS

Kominami, K.: 380 Komissarov, V.D. : 276 Konda, N. : 038

Kondo, A.: 190 Kondo, K. : 299 Kondo, T.: 070, 105, 111 201, 255 Konishi, M . i 023, 075, 261 Koreeda, M. 4 143, 336 Kornblum, N. 245, 279, 406

51 1

Kubota, H.:

080, 195 Kudaka, T.: 221 Kudo, K.: 156

Kula, J. : 057

Kulkarni, A.K.: 441, 454 Kulkarni, S.U.: 033 Kulkarni, J.S.: 431 Kulp, S.S. : 231 Kulp, T.: Kumada, ~.'P3D23, 027, 033, 075 Koser, G.F.: 446 205, 261, 341 Kumagawa, T. : 220 Koshiba, M.: 391, 442 Kumar, A.: 058 Koshino, H.: 354 Kumobayashi, H.: 389 Koshino, J.: 063, 290 Kumpf, R.J.: 489 Koskinen, A , : 351 Kunai, A. : 303 Kostantinovic, S. 056 Kunda, S.A.4 132, 455 Kostova, KI: 158 Kosugi , M. : 034, 127, 172, 228 Kunieda,,T. : 321 244, 391, 442, 467 KWZ, H. 4 017, 303 Kuran, W. : 154 Kotake, H.: 138, 42, 488 Kurata, Y.: 102 Kotelko, A , : 094 Kurihara, T. : 482 Kotera. M.: 151 Kurita, M.: 467 Koto, H.: 217, 331 Kurita, Y.: 234 Kotsuki, H. : 420, 091 Kuroda, H.: 307 Kowalski, C . J . : 004, 058, 152 Kuroda, K.: 085 450 Kuroda, T.: 284, 341, 349 Koyama, K.: 460 Kozikowski, A.P. : 069, 292, 370 KurOmaru, H,: 070 Kurosawa, K. : 369 480 KWUSU, Y.: 213 Kozlowski, J . A . : 076, 091, 092 K u s w t o , T.: 183, 342 Kozyrod, R.P,: 406 Kutaleladze,,A.G. : 367 Krafft, M.F. : 214 Kuwajima, I. : 092, 095, 147 Krantz, A. i 364 230, 319, 398 Kraus, G.A. : 152, 362, 453 * 465, 479 Kraue, H.W.: 037 Kuwajima, J. : 282 Krentzien, H.4 446 Kwart, L.D.: 353 Krepski, L.R. : 168 Kwasigroch, C.A.: 284, 373 Kress, J.:,255, 444 Kwast, A.: 435 Kresze, GI : 115 K w a t , E.: 435 K r i e f , A. : 065, 068, 092 Kwiatkowska, C. : 226 095, 166, 182 Kwon, H.B.: 111 193, 230, 258 Kwon, K.S.: 404 Krishnamurthy, S.: 097 Kyler, K.S.: 231 Krolikiewicz, K. : 11 7 Kyung, S.-H.: 025, 041, 406 Kryukova, Yu.1.: 016 Kyz'mina, L.G.: 478 KiikenhUhner, T.: 025

-

,

51 2

AUWORS

Labaudiniere, R. : 1 72 Laborde, E.: 419 Lacher, B.: 181 Lachhein, S.: 016 Ladlow, M.: 414 Ladouceur, G . i 065, 238 Laganis, E.D. : 008 Lai, R.: 446 Laidler, J . K . : 124 Laird, A.A.: 049, 361

Lakshmy, K.V.:

347

Lal, G.S.: 004 am, L.K.P.: 300 Lamatsch, B.: 318

Lamaty, G.: 026 Lambert, C. : 283, 368, 422 Lambert, J.B.: 094 Lambert, P.H.: 130 Lamed, R.: 037, 330

Lammer, 0.: 251 119 Lan, A.J.Y.: Lan, J . Y . : 080 Landgrebe, 152, 453 Landini, D. : 261 Landmann, B.: 024 Lang, R.W.: 417 Lardiccf , L.4 263, 282 Larock, R.C. : 073, 287, 414 415, 439 Larraza, M . I . : 408 Larsen, S.D.4 317, 384 Larson, G.k. : 257, 258 Laszlo, P. : 065, 078, 225, 225 226, 227, 230, 273 357, 431, 487 Lathbury, D.: 379 Lattes, A*: 132, 189 Lau, C.K. : 068 Laugal, J . A . : 487 Laughton, C.A.: 170 Laur, J.: 017 Laurent, A , : 392 Laurent , E. : 448 Laurent, H.: 185 Lautens, M.: 268 Lawesson, S.-0. : 102

K.:

INDEX

Lawrynowicz, W.: 190 Laycock, B.: 074 Lazaridis, N.V.: 355 LaBelle, B.E.: 323 Le Bigot, Y.: 253, 350 Le Goffic, F.: 353 Leach, S.J.: 077, 216 Learn, K.: 027 Leblanc, Y.: 265 Lee, H.S.: 044 Lee, J.I.: 136, 140, 142 152, 218 Lee, K.: 232 Lee, N.H.: 338 Lee, S.D.: 404 Lee, T . D . i 168 Lee, T.V. : 326, 402, 434 Lefker, B.A.: 479 Leftin, M.H.i 250 Lehmkuhl, H. : 268 L e i k a u f , U. : 320 Lemaire, M.: 158 Lennon, P. : 268 Leonard, D.: 145, 162 Leonard, W.R. 473 Leone-Bay, A.i: 229 465 Leong, W.W.H.: Leport, L.: 026 Lerman, 0.: 191 Lespagnol, C.: 247, 370 Lessi, A.: 001 Lesuisse, D. : 31 6 Leszczweski, D.: 306 Levenberg, P.A.: 481 Levkovskaya, G.G. : 01 6 Ley, S . V . : 426 LeGreneur, S.: 115 L i , W.S.: 184 L i c k , C.: 459 Lieberknecht, A. 194 Liebeskind, L.S.i: 090, 163, 293 Liebscher, J.: 244 Lin, J.-M.: 371 Lin, P.: 360 Lin, Y . J . : 414 Lin, Y.L.: 174

INDEX

L i n d e l l , S.D.: 031 Lindig, M. :,303 Lindley, 3 . : 076, i27, 173 Lindsay-Smith, J . R . : 190

LinstrumelJe, G.: 073, 454, 455 Liotta, D. : 164 Liotta, E.L.: $65 Lipshutz, B.H. : 076, 091, 092

361

Lisensky, $.A,: 441 Lissel, M . : 1'67 L i t t l e , R.D.: 401 L i u , H.: 140 L i u , H.-J. : 085 L i u , J . K . : 463 L i u , M.T.H.: 063 Livinghouse, T. : 147, 178, 473 Liz, R.: 205, 390 Lloyd, D.H.: 132 Lociuro, S. : 368 Lock, G.A.: 427 Lok, K.P.: 146 Long-Mei, Z . : 301 Lopez, C.: 054, 209 Lorenz, K . T ? . ~ 094 Loudon, G.M. i 116 Lounasmaa, M. : 351 Lovich, S.F.: 280 Liining, U.: 160 Lu, L.D.L.: 325 Lu, S.-B.: 266 Lucchetti, J,: 357, 431, 487 Luche, J.-L. : 060, 089, 107 Luehr, G.W.: 180 Luengo, J.I.: 336 Luk'yanets, E.A.: 094 Luke, R.W.A.: 366 L m a , P.K.: 380 Lwt, S.R.: 466 LuO,

51 3

AUTHORS

F.-T.:'206,280, 484

Lupo Jr.: A.T.: 371 Lusinchi, $.: 031, 123, Lutz, R.P. : 492 Lygo, B.: 426 Lyon, J.T. :,173 Lysenko, Z. : 354

259

P i a r k l , R.:

170

Mabury, S.A.: Macdonald, T. Lli'a 478 Machida, H.: 411 Mack, J.F.: 34p Macomber, D.W. : 473 MacFerrin, K.D. : 326 MacMillan, J.: 196 Maddaluno, J.: 459 Madyastha, K.M. : 1 20 Maeda, K.: 337 Maeda, N.: 318 Maekawa, E.: 399 Maekawa, T.: 287 Mafunda, B.G.: 073 Magnin, D.R. : 229 Magriotis, P.A.: 209 Mai, K. : 242, 385, 386 Maienfisch,,P. : 403

Maier, W.F. : 198

Maigrot, N.: 234 tlaione, A.M.: 024 Majchrzak, M4W. : 094 Majetich, G. : 087, 422 Mak, K.T.: 380, 387 Makabe, Y. :,360 Makosza, M. : 435 Malfroot, T.: 121 Malmberg, H.: 127 Mamada, A.: 246 Manabe, H.: 122, 135 Mandai, T.: Q03, 009, 461 Mandal, A.K. : 142 Mander, L.N.: 402 Mane, R.: 409 Manescalchi, F.: 028, 183, 463 Mangeney, P. : 089 Mangoni, L.: 157 Manitto,,P.: 233 M a , G. : 108

Manna, S.: 185, 349 Manoharan, T.S.: 120 Mansuy, D . : Mantanari, F:!' 010 Marais, D.: 353 Marcano, M.M. : 491

514

AUTHORS

Marchand-Brynpt , J. : 1 01 Marchelli, R4 : 449 Marchese, G. 089, 206, 209 Marcos, M.: 3i8 Marcuzzi, F.: 002 Maresca, L.: 276 Harherbe , R. :,154 Mariano, P.S. : 119, 390 Marinelli, Fa: 348 Marino, J.P. : 399, 419 Marquet, J. : 462 Marra, J.M.: 134 Marrero, R.:,392 Marsi, M.: 441 , 470 Martelli, G.: 028, 109 Martin, A.: 230 Martin, J . C . : 382 Martin, M.G.: 259 Martin, O.R.: 298 Martin, S.J.: 286 Martinez Alvarez, R.: 080, 456 Martinez-GalJo, J.M. : 448 Martinez, J. : 017 Martz, J . T . i 121 Maruoka, K. : 038, 039, 064, 096 122, 128, 129, 192

-

326, 339, 485 318, 343, 396 489 Masamune, S.*: 010, 044, 150 322, 350 Mason, R.: 257 Massardo, P.: 485 Masset, P.: 3#9 Mastalerz, H. : 018 Masters, N.F.: 077, 2 6 Mastorilli, E.: 447 Masuda, M.: 410 Masuda, R. : 028, 065, 080 Masuda, T.: 398 Masuda, Y.: 139, 246, 289 Masunga, T. : 465 Masuyba, A.4 434 Masuyama, Y. : 210, 213 Mather, A.N.: 030 Mathy, A . : 078, 226 Maruyama, K.:

INDEX

Matsubara, S.: 012, 159, 334

345, 347, 357

Matsuda, A.: 398 Matsuda, H.4 344 Matsuda, I. : 337, 475, 482 Matsuda, T.: 078 Matsumiya, K.: 229 Matsumto, H.i 071 Matsumoto, K. : 075, 376, 383

*

396 023, 252, 308 466 Matsumoto, T.: 038, 128, 183 336 Matsumura, N.*: 302 Matsumura, Y.: 103, 129, 217 118 -Matsuo, T.: 189 Matsuoka, H.: Hatsushita, H.519022, 040, 072 Matsuura, T.: *305, 356, 397 Matteso, D.S. i 045 Matteson, D.S. : 175, 346 Maumy, M.: 195, 208, 466 Maus, S.: 024 Mazur, D . J . : 444 McBride, B.J.; 173 McCarthy, K.E.: 091 McClure, C.K. : 444 McCollum, G.W.: 132 McCoy, R.K.: 359 Matsumoto, M.

:

McDermtt, S.D.: 112 McGarry, D.G.: 100 McGee, M.J.: 231 McGuire, M.A.: 365 McKean, D.R. : 436 McKeer, L.C.: 190 McKenna, J.: 241 McKervey, M.4. : 228, 429, 464 McKillop, A. : 247, 274, 275

393

McMaster, D. :*OO6McMurry, 3.E. : 223, 267 McNab, H. :,382 McNelis, E. :,403 Mechoulam, R. : 427

INDEX

AUT'HOFS

Mehrota, 4.K.: 011, 182 Mehta, G. : 449 Mehta, P.G.: 347 Meier, G.P.: 382 Meier, M.: 247 Mei j e r , J. : 438 Meist.er, A.: 304 Melany, M.L.i 427 Mellor, J.M. : 110, 278 Meltz, C . N . : 179 Mendoza, L. : 121 Menichi, G.: 241 Menoret, G.: 220 Mera, A.E.: 489 Merrifield, J.H. : 472 Mert.ens, A,: 435 Metra, P.: 078 Metzger, J.i 446 Meunier, B. * 177 Meyer, G.: 2iO Meyers, A.I. : 063, 119, 122

Minami, I.: 117, 212, 405

515

417, 421, 466 472, 474, 478 479, 480, 483 t191 Mincione, E. : 159 Minobe, M. : 404, 345 Mioskowski, C. : 185, 436, 439 Miranda, E.I.: 066 Mirskova, A.N.: 016 Misawa, H.: 290, 360 Mishra, P.: 138 Misintsev, V.V. : 464 Misiti, D.: 237, 275 Mison, P.! 392 Misu, D.: 215, 221, 289 Mita, T.: Q84, 342 Mitani, M. i 460 Mitsudo, T. : 001, 290, 423 M i t s u i , H.: 274 Mittal, R$.: 274 134, 321, 404, 479 Miura, M. : 222 Michael, J . P . : 383 Miwa, T.: 334 Michelotti, E.L.: 068, 071, 250 Miyake, H. : 433, 484 Miginiac, L. 420, 442 Miyake, J.: Miyasaka, T.'T9218 Miginiac, e.*I 381, 488 Miyashita, M.: 303 Migita, T. : 034, 127, 172 Miyaura, N.: 076, 176, 490 199, 228, 244 Miyazaki, M.: 084 391, 442, 467 Miyazaki, T.: 129 Mihailovic, M.k.*: 056 Miyazaki, Y.: 345 Mihelich, E.D. : 467 Miyazawa, S.: 377 Mikaelian, G.S.: 478 Miyoshi, N . : 010 Mikami, K.: 029, 249, 340 Mizuguchi,,Y.: 203 Milenkov, B.: 409 Mizuno, K. : 483 Milesi, L.: 261 Mizusaki, S.: 022, 040 Miller, D.D.: 223 Mizuta, Y.: 212 Miller, J . A . : 206, 289, 468 Mizutani, M.: 400 474, 488 Mobbs, B.E.: 170 Miller, R.D.*- 436 Moberg, C.: 422 Miller, R.O.*: 439 Modena, G.: 276, 492 Mills, S.: 11; Moghaddam, M.E.: 213 Milstein, D. : 023, 082 Mohajer, D.:,213, 214 Mimun, H.: 177 Mohamadi, F. : 151, 265, 309 Mohan, R. : 407 Mohler, D.L.: 427

51 6

INDEX

AUTHORS

Moison, H.: 09Q Molander, G.A. : 041, 073, 076 224, 283, 322

*

323, 339, 470

Molina, P. : 034, 149 Molinari, H.: 436 Molinski , T.F. : 329 M O ~ O K ~ ~ O VA.N.: ,

464

Morisaki, Y.: 003 Morita, T.: 203 Morita, Y.: 086 Morizawa, Y.: 204, 250, 269

334, 345, 405 061 21 3 081 294 029, 046, 049 179 Morton, J . A . : 381 Mortreux, A , : 254 Moskal, J. : .061, 471

Pforizur, J.-p.: Moro-Oka, Y. : Morrissey, MIM.: Morrow, C . J . Morton, H.E.*I

Momosi, D. : 071 Monaco, P.: 157 Monkiewicz, J. : 477 Monkovic, I.: 123 Monobe, H.: 218 Montanari, F.: 311 Montanucci , M. : 171 Mostaf'avipoor, ZI: 211 Monte, W.T.: 401 Motherwell, W.B. : 115, 129, 181 Monteil, T.: 351 194, 234, 385 Motherwell, WIJ. : 460 Montes, J . R . : 379 Montevecck$, P.C. : 380 Motohashi, S. : 338, 409, 428 Monti, D. :,233 Mourad, M.S.: 233 Moody, C . J . : 154 Mouzin, C. : 426 Mook Jr.: R.: 162 Moya-Portdguez , M. : 1 01 Moore, D.W.: 346 MUler-Starke, H.: 245 Moore, J.L.: 396 MUler, P.: 052, 275 Moore, L.L.: 317 Miinsterer , H. : Moracci, F.M. 365 Muchowski, J .V. 5~67 Morales, H.R.i: 121 Mukaiyarna, T. : 010, 047, 048 Morand, P.: 056 088, 141, 168 Mordini, A . : 229 201, 320, 345 Morella, A.M.: 401, 447 407, 416, 431 Morellet, C.: 312 432, 433, 461 Moreno-Manas, M. : 462, 485, 4.91 467 Morera, E. : 202 Mukerji, I.: 032 Moret, E.: 348 Mullican, V.D.: 395 Moretti, R . : 297 Mulzer, J. : g51 Mori, A , : 038, 096, 287 Murahashi, S. : 124, 274, 360

'1

326, 454

Mori, I.: 343, 358 Mori, K.i 277, 316 Mori, M. : 107 Mori, S.: 126, 156 Mori, T.: 020, 051, 207, 321 Mori, Y.: 411 Moriarty, R.g. : 238, 333, 335 Morimoto, T. : 126, 211, 353 Morisaki, K.: 013, 070

Murahashi,

*

s.-I.'~~Ios, 247, 355 389

Murai, S. : 058, 077, 092, 097

170, 235, 259, 426 426, 428, 458 Murai, T. : 131, 170, 426 Murakami, M.: 047, 048, 416 462 Murakami, T.: 211

*

INDEX

AUTHqRS

Murakami, Y.*: 075 Murata, T.: 445 Murayama, 8.: 219, 266, 476 Murota, K. : 398 Murray, S.: 065, 238 Muruoka, K.: 129 Muruyama, 5 . : 075, 391 Muzart, J. : 216, 374, 423, 481 Myles, D.C.:,326 NBsw, J.H. : 366 Naderi, M.: 054 Naef , R.: 091 , 296 N a f t i , A . : 392

Nagao, Y.: 212, 359 Nagaoka, H.: 048 Nagasaki, N.: 015 Nagashima, E.: 310 Nagashima, H.: 078, 232 Nagasuna, K.: 232 Nagata, R.: 305, 397 Nagata, SI: 107, 157, 418 Nagel, U. : 084 Nagusa, H.: 104 Naim, S.S.: 407 Najera, C.: 110, 308, 370, 448 Naka, K.: 394 Nakagawa, I.: 327 Nakagawa, T.: 015, 116, 144

366

Nakagawa, Y.: 290 Nakahama, S.: 036, 038 Nakahara, Y.: 184 Nakai, K.: 113 Nakai, S.4 064, 192 Nakai, T. : 029, 283, 340 Nakajima, N.: 247 Nakajima, T.4 009, 309 Nakamura, A.*: 232, 337 Nakamura, E. : 147, 230, 319

398, 465

Nakamura, H.: 243 Nakamura, K. : 1 98 Nakamura, N.: 129 Nakamura, T.: 408 Nakanishi, A.: 160 Nakano, M.: 038, 127

51 7

Nakano, T.: 039, 311 Nakao, K.: 014 Nakashi t a , ,Y. : 458 Nakata, T. : 042, 043, 307 Nakatani, H.: 078 Nakatani, K.: 472 Nakatani , M. : 304, 369 Nakatani, Y.: 287 Nakatsuka, T.: 412 Nakatsukasa,,S.: 284, 328, 417 Nakayama,*J. : 411 Nambu, Y. : Namy, J.L.:

248 024, 220, 307 Nanbu, H.: 345 Naota, T.: 109, 247, 389 Napolitano, E. : 447 Narang, S.C.4 047, 192, 246 Narasaka, K. : 309, 310, 315 3 9 , 334, 345 Narasimhan, N.S. : 042, 128 Narayana, C. : 232 Narayanan, K.: 073, 414 Naritomi , M. : 078 Narula, C.K.: 380, 387 Naruse, X.: 433 Naso, P. : 089 Natalie Jr.: K.J.: 478 Natarajan, S.: 471 Natile, C.: 275, 276 Natsugari, H.: 375' Nazasaki, N.: 144 Nazer, B. : 051 Ndebeka, C.4 462 Negishi, E. : 006, 072, 206, 206 280, 407, 441, 468 474, 484, 488 Negishi, Y.: 244

Negoro, K.: 052 Nemo, T.E.i 177 Nmoto, H. : 232 Neubert, M.E.: 014 Neunann, B . i 167 Nemann, 8. : 011 New, J.S. : 131 Newington, I.M.: 097, 352 Newton, T.W.: 438

518

Nguyen, S.L.: 991 Nicholas, K.MZ : 280 Nichols, D,E. Nickon, A. : Nicolaou, K.C?

*

132

Niessner, M. : 285

184

Nikam, S.S.: 481 Nikishin, C . I . : 464 N i k i t i n , Yu.E.: 276 N i k u l i n , A.Y.: 367 Nilsson, M. : 127 Nimmesgern, H. : 103

Nisar, M.: 228, 479 Nishi, S.: 477 Nishida, T.: Nishiguchi, I?? 057, 467 Nishihara, H.: 211 Nishimoto, S.: 120 Nishina, H.i 240 Nishino, H. :,369 Nishiyama, H. 252, 308, 481 Nishiyama, K.*I 125, 240 Nishizawa, M.: 037 Nitta, K.: 458 N i w a , H.: 216 Noels, A.F.: 093 Noguchi, S.: 218 Nohira, H.i 026 Nokami, J. : 235, 344 Nornoto, T.: 248 Nomura, M . i 222 Nonaka, T. : 143, 328 Nordberg, R.E.: 415, 416 Norisue, Y.: Normant, J.-F!'i) 073, 089, 173 208, 220, 389 415, 454, 455

-

486 Nowak, M.Al.: 208, 304 Noyori , R. : 037 Nozaki, H.:

INDEX

AUTHORS

066, 208, 263, 324,

097, 159, 204 214, 250, 251 266, 269, 284

334, 341 8 343 345, 347, 349, 358 405, 417, 422, 476

Nozaki, Y.:

-

141 Nudelman, A. 440 Nugent, W.A.*: 487 Nunmoto, S.*I 072 Nutaitis, C.F.: 021, 327 Nystrm, J.E.: 125 O'CoMor, B.: O ' D O M e l l , M.J?; 297

O'Malley, G.J.: 397 O'Reilly, N.J.: 330 Obayashi, M.: 342, 425 Obrecht, R.: 242 Obrzut, M.L.: 161 Obushak, N.D.: 400 Ochi, M.: 020 Ochiai, H.: 207, 220, 364 398, 408, 471 Ochiai, M.: 212, 267, 357, 359 Oda, D.: 270, 388 Oda, H.: 204, 269 Oda, 1.i 388 Oda, M. : 076 Ogata, M.: 199 Ogata, T.: 172 Ogawa, A,: 259, 458 Ogawa, H.i 300, 391 Ogawa, M. : 039, 211, 311 Ogawa, S.: 236, 327 Ogawa, T.: 190 Ogawa, Y. : 048 Ogibin, YIN-: 464 Ogura, F.*: 135 Ogura, K . : 009, 351, 358 Ohannesian, L.: 226, 449 Ohashi,.Y.: 117, 223, 418, 474 Ohhara, H.: 253 Ohhashi, K. : 034 Ohira, N.: 135 Ohishi, M. : 336 Ohki, H.: 345 Ohmura, M.: 488 Ohno, A . i 198 Ohno, M. :,277, 316 Ohsawa, T. : 119, 203 Ohshim, M.4 010, 047, 048, 416 Ohshiro, Y. : 188, 465

INDEX

AUTHORS

51 9

180, 269, 270, 349 412, 417, 475 Oohashi , M. : 124 Ookawa, A.: 845, 090 Oppolzer, W. : 089, 090, 297 372, 412, 413, 492 Orena, M.: 314, 332 307 Oriyama, T.: 201, 320, 345 Ortar, G. : 202 Ojima, I. : 1 1 1 Ortuno, R.M.: 491 Oka, S.: 043, 198 3saka, N.: 481 Okada, H.: 482 Osakada, K.: 144 Okada, M.: $77 Osawa, T.: 106 Okahara, M. 434 O s b r n , J.A.: 255, 444 Okamoto, T.*I 043 Osby, J.O.: 234 Okamoto, Y . : 261 Oshikawa, '6. : 184 Okano, K.4 113, 353 Oshirna, K. : 097, 204, 208 Okano, M. : 181 214, 250, 251 Okawara, M.: 144, 211, 272 263, 266, 269 345, 448 284, 324, 328 Okawara, R . : 344 334, 343, 345 Okazaki, M.E.: 138, 382 347, 349, 357 O k a z a k i , R. : 104, 122, 386 358, 405, 417 Okame, T.: 347, 476 Oshino, H.: 147, 398 Okinaga, N.: 1 1 1 Ostarek, R.: 024 O k i t a , M.: 107 O k i t a , M.: 363 Osugi, J.4 383 Osuka, A. : 080, 167, 189, 195 OkonkwoJ, J.O.: 402 201, 204, 243, 270 Oku, A. : 032, 093, 271, 327 333, 411, 481 341, 443 Oswell, K.D.: 124 Okuda, Y.: 097, 208, 250 Otani, S.4 376, 383 251, 417 Otera, J. : 003, 009, 047, 066 Okukado, N.: 280 327, 360, 461 Okumoto, H.: 151 Otsubo, K . : 147 Okumura, HI: 129 Olah, G.A. : 01 1 , 047, 108, 175 Otsubo, T.4 135 182, 189, 191, 192 O t s u j i , Y. : 044, 483 226, 244, 246, 302 O t s u k a , H . 4 076 Otsuka, S. : 389 435, 449 O t t , W.: 164 Olano, B.: 385 Ottana, R.: 002 Olofson, R.A, : 121, 187 Omori, K.: 284 Ou, K.: 133 Ousset, J.B.:,436, 439 Omura, H. 235 Overrnan, L.E. : 106, 131, 138 Onaka, M.i: 165 316, 382, 388 Onishi, 360 44'3. _ . 492 Onka, M. : 444 Owa, M.: 038

O h s u m i , T.: 105, 135, 467 Ohta, H.: 141 Ohta, M.: 334 Ohta, T.: 101, 135, 388 Ohtani, B.: 12C Ohtsuka, H.: 043 Oikawa, HI: 098 Oishi, T.*: 042, 043, 203,

0

x.:

Ono, N.*:

520

INDEX

AUTHORS

Oyamada, H. : 036, 037, 318 OzaKi’, J.: 490 Pac, C . : 128 Padmanabhp, S.: 280 Padwa, A. : iO3, 270 Page, P.C.B. : 408, 451 Paget, W.E.: A91 Pagnoni, U.M. : 452 Pai, F.-C.: 310 Pai, G.G.: 320, 329 Paisley, 2.D.: 070 Pak, C.S. : 086 Paknikar, S.K.: 175, 178 Palla, F.: 282 Palmieri, G.: 237, 275, 276 Palmino, E . i 291, 350 Palomo, A.k. : 099 Palomo, C . : 054, 185, 187

* 209, 240, 448 Panunzi, A. i 343 Panunzio, M. : 028, 109, 183 Papadopulos , K. :,353, 402 Papaleo, S.: 229 Papini, A.: 313

Paquette, L.A. : 320 Pardo, S.N.: 414 Park, K.B.: 022 Park, W . S . : 319 Parker, D.A.: 091 Parkhurst , C .S. : 437 Passarotti ,,C. : 085 Pasto, D . J . : 271 Pastorelli, S.: 229 Patel, D .D. :,226 Paterson, : 175 Pathak, T. : 055 P a t i l , G.: 242, 385, 386 P a t i l , P.A.: 042 Patricia, J.J,: 074 Patrick, T.B. : 400 Patrie, W . J . : 143 Patt, H.: 153, Pattenden, G. : 212, 414, 444 Paudler, W.W.: 210 Pauluth, D.: 055 Pauly, M.: 247, 370

&.

Pavlov, S.: 059 Pazynina, G.V.i 094 Pearlman, B.A. : 267 Pearson,.A.J.*: 402, 415, 455

*

470, 475

Pearson, W.H. : 124, 392 Pearson, W.W. : 098 Pedrosa, R.: 297 Peevey , R .M. :,374 Pellacani,,L. : 368 Pelter, A. : 033, 114, 264, 308 Pena, M.R.: 419 Pennetreau, P.: 065, 230, 273 Peretz, M.: 004 Perez- Juarez ,,M. : 1 21 Periasamy, M. : 232 Perichon, J.: 013, 026, 222

260

Perie, J.J.: 132 Perni, R.B.: 241 Perrone, E.: 018, 185 Perry, D.A.: 21g, 444 Perry, M.W.D.: 234, 352 Perry, R . J . : 469 Perumal, P,T. : 044, 344 Pete, J.P. : 198, 374, 423, 459 Peter, R.: 024, 025 Peters, E.-M.: 146 Peters, K.: 146 Petersen, J.S.: 044, 350 Peterson, J.R.: 161, 162, 393

419, 446

Peterson,,R.T. : 394 P e t i t , F. : 254 P e t i t , M.: 254 Petraglia, S.P.: 075 Petragnani, N.: 005, 286 P e t r i e r , C.: 089 Petrignanil, J.-F.: 226, 446 Pews, R.G. : 354 Peyton, K.B.:,450 Pfenniger, A.*: 329 P f i s t e r , J . R . : 113 Pfluger, F.: 013 Phillips, B.T.: 380 Piccardi, P,: 485

INDEX

AUTHORS

Piccolo, o.*: 313 Pichon, C2: 167 Piers, E. : 250 Pietre, S.: 068 Pietrusiewicz, K.M. : 477 Pigiere, C.L.: 376 Pigiere, Ch.: 363, 378 P i k e , d . : 988 Pindur, U. : 356

,

Pinhas, A . R . i 291 Pinkey, J.T. i 406 P i n n i c k , H.W. : 101 Pinsker, O.A.: 197 Pinto, A.C;: 399 Piotrowski, A&: 264 Pirrung, M.C. : 434 Pitchen, P.: 276 Piteau, M.: 121 Piva, 0.: 423 P l a u t , H.: 045 Plenat, F.: 376 Plessi, L.: 028, 183, 463 Pltlmer, R; : 186

Pluscec, J.: 471 Pogorzelska-Marciniak, B. : 154 Poirier, J.-M.: 451, 459 P o l i , C.: 090, 310 Polishchuk, O.P. : 400 Poll, T. :,306 Polla, E. : 109, 225, 227 P o l l i n i , C.P.: 471, 483' Polywka, M.E.C.: 171 Pong, R.Y.: 096 Ponomarev, A.B.: 001, 221 Poon, Y.-F.: 392, 400 Pornet, J.: 420, 442 Portella, C . i 198 Porter, N.A. : 229 Porzi, C.: 322 Posner, C.H. : 021, 088, 170 266, 428 Poss, M.A. : 360 Potenza, J.C.: 350 Potnis, S.M.: 461 Poupart, M.A.i 063 Pradhan, S.K. : 043

521

Prager, B. : 322 Prahash, I.: 333 Prajapati, D.: 385 Prakasa Rao, A.S.C.: 173 Prakash, C.K.S.: 226, 449 Prakash, 0.: 238, 335 Prandi, J.: 177, 220 Prasad, G.: 291, 350, 478 Prasad, J.J.N.V.: 317 Prasad, K. : 322 Prat, M.: 491 Pratt, D.V.: 363

Previtera,

k.:

157

Pri-Bar, I. : 202, 248 Price. M.F.: 469 Price, T.: 08 Procter, C. 030 20 Pugin, B.: Purr i n g t on, S.T.*: 355, 429 P u t t , S.R.: 267 Quabeck, u. 266 Quader, A , : 077 Quadri, M.L.: 261 Qudllich, C.: 430 Q u i l l e n , S.L.: 119 Quinn, N.K.: 075 Quintard, J.-Psc: 384, 460 Rabinovitz, M. : 261 Radhakrishna, A.S.: 115, 116 Rafizadeh, K.: 168 Ragnarsson, U. : 138 Rahamim, ,Y. : 082 Rahn, A. : 040 Rahn, B.J.: 073 Ra jagopalan, S. : 457 Raju, N.: 169 Rakiewicz, D.M.: 306 Ram, S.: 135, 378 Ramachandran, J.: 017 Ramadas, S.R.: 017 R a ma n , K.: 403 Ramani , B. : 085 Rambaud, M. : 168, 420 Rampi, R.C.: 126 Rand, C.L.: 072 Randriamahefa, S.: 012

522

AUTHORS

*

INDEX

Ricard, M,: 096 Rao, A.S. : 166, 175, 178 Ricci, A. : 229, 313, 315, 336 Rao, C.G.: 115 Ricci, M.: 176 Rao, C.T.: 031, 456 Rice, E.M.: 075 Rao, H.S.P.: 449 Richards, I.C.: 402 Rao, V.B.: 219 Richardson, K.A.: 326, 434 Rappa, A.: 032,,487 Richardson, S.: 360 Rasmussen, J . K . : 168 Richey Jr.: H.C. : 083 Ratananukul ,,P : 464 Rathke, M.W. : 208, 304 Rico, I.: 189 Rathore, R . : 160, 21 3, 238 R i d e l l a , J . i 224 Ratovelomanana, V.: 073, 454 Rieke, R.D. : 071, 206, 245 455 340 Raucher, S. : 137, Rieker, W.F.: 122 Riepel, G.: 036 Rautenstrauch, V. : 469 Rieu, J.-P.i 426 Ravenscroft, P.D.: 219 Rigby, JIH. : 046 Ram-Petersen, L.S.: 468 Rim, B. : 247, 370 Ray, T.: 470, 475 Riguera, R.*: 368 Razintsky, M.: 292 Rimpler, M. : 450 Reagan, J.: 026 Ringer, E.: 020 Rebrovic, L.: 446 Riondel, A.: 462 Reddy, D.B.: 093 R i s t , G. : 154 Reddy, N.P.: 054, 210 Rivera, A,D.: 396 Reed, J . N . :,361 Reetz, M.T. : 024, 025, 041, 079 Rasch, L. i 086 209, 227, 245, 329 Robert, A. : 401 332, 340, 404, 406 Roberts, J X . : 010 Robinson, B.L.: 447 474 Regen, S.L. : 164 Robinson, P.L.: 166 Rocherla, U.S. : 283, 288 Regenye, R. : 325 Roder, H.: 146 Regondi , V. : 171 Rodriguez, A.D.: 440 Reibenspies, J.: 298 Rodriguez, M.A.: 457 ReibenspiesZ J.H.: 310 Rodriques, K.E.: 367 Reich, H . J . : 301 Roggo, S.: 025 Reimer, C.J.: 061 Rokach, J.: 165, 382 Reinking, P.: 165 R o k i c k i , G.: 154 Reissig, H.-U. : 152 Rolmdo, C.: 064 Remuson, R.: 363 Rolla, F.: 261 Renaud, J.-P,: 177 Rollin, Y1: 260 Renaud, R.N. : 383 Romeo, A. : 054 Rendenbach,,B.E.M.: 353 Romeo, G.: 002 Renga, J.M. : 165, 301 Ronald, R.C.: 254 Repic, 0. : 322 Rondrianielina, B. : 442 Restelli, A.: 311 Ronzini, L.: 989, 206, 209 Reuman, M.: 063 Rosenblum, M. : 108, 268, 470 Rhee, I.: 235 Rosenthal, S.: 408, 451 Rheingold, A.L. : 387

.

*

*

INDEX

523

AUTHORS

Roskamp, E.J.: 434 ROSS, B.A.: 116 Rosser, R. : 308 Rosser, R*M.: 114 Rossi, R. : 001, 281 Rossini, G.: 336 Roth, Z.: 440 Rouessac, F.P.: 299 Rousseau, g. : 094, 420 Roussi, G. : 118 Royer, J.4 133 Rozen, S. : 178, 191, 450, 452 Rlichardt, C. :,247 Rubottm, G.M. : 392 Rudham, R.: 212 R u d i s i l l , D. : 01 4 Ruggeri, R.: 444 Russell, C.E. : 468 Russell, D.N.: 228 Russell, J.J.: 212, 444 Ruzziconi, R.: 394 Ryabov, V.D.: 067 Ryang, M.: 235 Rychnovsky, S.D.: 162 R y u , I.: 097, 092, 235, 458 Sabadie, J.: 020 Sabirov, S.S.: 432 Sablukova, I.: 037 Sabol, M.R4: 405 Saburi , M. : 144 Sadhu, K . M . i 175 Saednya, A. 242 Saegusa, T.*i 356, 380, 435 1

477

Saeki, S.: 235 Sahai, M.: 440 Sahlberg,,C.: 077 Saigo, K. : 236 Saindone , M. : 1 64 S a i t o , E . i 109 Saito, I. : 305, 397 S a i t o , M.: 240 S a i t o , Y.: 343 Saitgh, T.: 203 Sakaguchi* H. : 252 Sakai, K . : 460

Sakai, S.: 153, 160, 473 Sakaitani , M. : 076 Sakakibara, Y.: 303 Sakakura, T.: 230, 378 Sakane, S.: 128, 129, 485 Sakane, T.: 131 Sakata, K.: 220, 384 Sakata, Y.: 377 Sakdarat, S,: 046 Sakurai , H. : 044, 064, 237 377, 430, 443 453, 472 Sakurai, K.: 039 Sakurai , M. : 039, 064 Sakurai, Y.: 286 Sakuta, 481 Sala, R. : 085 Salama, P . i 172 Salaun, J. : 253 Salazar, J.A.: 182 Saleh, S.A. :,346 S a l l a d i e , G. : l?tr S a l o ~ M.F./ , 414 Saloman, R.G. : 414, 479 Salunkhe, M.: 409 Samayaji, V . i 453 Sammes, P.G. : 121 Sampson, P.: g24 Sanchez, I.H. : 408 Sanda, F.: Sandhu, J.S.2g? 385 Sandison, M , : 291 , 350 Sandler, J.: 254 Sa ndri , 314, 332 Sano, H. : 034, 122. 172 192, 199, 244 345,,391, 442 Santaniello,,E. : 060 S a n t e l l i , M. : 281, 303 S a p r i t o , A.: 343 Sardarian, A.R.: 054 S a m , D.N.: 154, 198, 252 Sarma, J.C.: 154, 252, 425 Sas, W.: 278 Sasaki , K. : 266, 303, 430 Sasaki , M. :. 467

4.:

9.:

524

Sasaki, T.: 277, 316 Sasakura, K.: 335 Sasatani, S.: 129 Sassaki, K,: 064, 237 Sasson, Y. : 011, 035, 292 Sastry, K.A.R.: 453 Sastry, V.V.S.K. : 017 Satish, #.V.: 461 Sato, F. : 248, 439 Sato, K.: 044, 151 Sato, M.: 097, 204, 248, 266 Sato, N.4 195 Sato, R. : 240 Sato, S . i 337, 475 Sato, T. : 008, 020, 044, 051

068, 184, 207, 219 234, 250, 266, 322 341, 425, 441, 476 * Sato, Y . : 127, 239 Satoh, J.Y.: 302 Satoh, T.: 220, 237, 338 384, 409 Satoh, Y.: 354 Satomi, M. : 428 Satyamurthy, N.: 193 Sauerwald, M.: 209 Savoca, A.C.: 034 Savoia, D . : 319 Sawahata, M. : 342 Sawaki, Y.: 012 Sawamura, M. :,299, 380 Sawicki, R.A. : 155 Sawyer, J.S.: 478 Sayo, N. : 283 Scallen, T.J.: 294 Scanga, S.A.: 333 Scanlan, T.$.: 445 S c e t t r i , A. 4 252 Schaap, A.P. : 291, 350 Schamp, N . 4 130, 318, 381 Schank, K. : 459 Schauder, J . R . : 258 Scheibye, S.: 102 Scheigetz, J.: 068 S c h i a v e l l i , M.D.: 427 Schiess, M.,3?2, 383

INDEX

AUTHORS S c h i l l e r , A . 4 186 Schinzer, D. : 088, Schlessinger,,R.H. : 360 Schlosser, M. : 348 Schmid, J.: 170 Schmidt, S.4 167 Schmidt, U . : 194 Schmidtberger& S.: 332 Schneider, F.*: 339 Schneider, M. : 300

Schnur, J.M. : $81 Schtillkopf, U. : 377 Schobert, R.: 222

Scholl, B.: 169 Scholler, 198, 459 Scholz, D. : 274, 271, 429 Schreiber, S.L. : 026 Schroeder, J.E.: 032 Schultz, F.W.: 346 Schultze, L.M.4 365 Schuster, C.B. : 080 Schwartz, E.4 444 Schwartz, J. : 254, 437 Schwellnus, K . 4 404 ScolasticQ, C . : 310 S c o t t , F. : 073 S c o t t , W.J.,262, 419 Scripko, J.: 370 Seamon, D.WI: 427 Seebach, D. : 025, 045, 296

8.:

308, 312, 318 335, 346, 375, 383 Segoe, K.: 435 S e i t z , S,P.: 048 Seki, Y. 077 Sekiya, M:*: 113, 126, 276, 310 ,353,362, 377 Seko, T.: 399 S e l f , C.R.: 469 Selikson, S.J.: 231 Selim, A.: 150 Selle, B.$.: 446 Selve, C . : 133 Sernenovskii, A.VI : 197 Semmelhack, M.F. : 053, 413, 437 463, 482

-

INDEX

AUTHORS

Senaratne, K#P.A.: 357 Senet, J.-PA : 121, 136 Sennyey, G. : 136 S e r a g l i a , R.: 276 Serebrenni kova, G. A. : 052 S e t , L.: 231 Seth, K.K.: 037, 330 S e t h i , S.P.: 402 Seto, K.: 410 S e t z e r , A.: 451 Seyferth, D. : 397, 461 Shabarov, Yu.S.: 141 Shadday, J . : 165 Shafikov, N.Ya.: 276 Shahriari-Zavareh, H.: 037 Shanklin, P . L # : 424 Shanmugam, P. : 012 Shapiro, M.J,: 322 Sharma, R.P. : 047, 154, 179 198, 252, 425 Sharp, M.J.: 102 Sharpless, K.B. : 293, 297, 300 312, 314, 316 325, 328 478

Shashkov, A.S.: Shea, K . J . : 410 Shea, R.G.: 295, 372, 374 Sheets, R.M.: 210 Sheffy, F.K.: 074 Shellhamer, D. F. : 447 Shen, Y.: 055, 419, 423 Shen, Y.C.: 040 Sher, P.M.: 436 Shereshovets, V.V. : 276 Sheth, J.P.: 093, 347 S h i , L.: 359, 380 Shibasaki, K. 009 Shibasaki, M.': 048 Shih, J.: 302 Shih, J . G . : 189, 191 Shim, S . C . : 145, 196 Shima, K.: 128 Shimada, J.: 465 Shimasaki, Y.: 307 Shimizu, H.: 270, 411, 455

525

Shimizu, I.: 117, 212, 223

228, 387, 405 417, 418, 466 472. 474, 480 483. . . Shimizu, M.*- 095, 184, 318, 431 Shimizu, N.*i 188 Shimoji, K . : 235 Shinoda, K. : 192 Shinozaki, 8. : 239 S h i o i r i , T. : 126, 482 Shiota, T.: 274 S h i r a i , F.: 283 S h i r h a t t i , V.: 440 Shirouchi, Y.: 159 Shobara, 012 Shono, T. : 103, 104, 111 217, 338, 467 Shrock, R.R. : 255 Shroff, H.N.: 117, 377 Shubert, D.C.: 073, 076 Shustermp, A . J . : 180 Shvo, Y . : 082 S i b i , M.P.: 027 S i b i l l e , S.: 026, 222 S i b t a i n , F.: 195, 226 Siddiqui, S.: 291, 350

v.:

S i d l e r , D.R.: 378 S i d o t , C . : 011 Siegneier, R. : 01 7 S i h , C . J . : 042 Sikorski, J . A . : 002 Simon, E.S.: 129, 385 Simon, R.: 339 Simons, R.W.: 366 Simpson, T.H.: 427 Sims, J.J.: 404 S i n c l a i r . P.J.: 298 Singaram, B.: 033, 044, 264 Singh, Singh, Singh, Singh, Singh, Singh,

470

A,*: 281 B.B.: 115, 120 B.P.: 011, 182, 189, 191 H.K.: 245, 279

S.M.: 283, 288 S.P.:

339

526

AUTHORS

Singh, V.: 230 S i n g l e t o n , D. HI: 429 Sipe Jr.: H . J . : 273 Sivavec, T.M.: 019 S j o g r e n , E.B.: 313 S k e l l , P.S. : 190 S k e t , B.; 186, 449 Slough, G.A.: 161 Slougui, N.: 094, 420 S l u s a r s k a , E . : 113 Smegal, J . A . : 178 Smeret, G.: 218 Smigielski* K.: 057 Smit, W.A. : 478 Smith 111, A.B. : 416, 481 Smith, D . J . H . : 104, 156 Smith, 1.J.i 049 Smith, J.2. : 033, 075 Smith, K . :*191 Smith, M.B. : 116, 117, 126 ,182,

261, 377

Smith, R . A . J . : 061 Smith, S.: 121 Smith, T.L. :,455 S n i d e r , B.B. 223, 407, 431 Snieckus, V.": 027, 103, 361 Snyder, J . K . * i 309 So, J . H . 4 445 S o a i , K. : 036, 037, 045

-

090, 318, 330

Sobczak, A , : 306 Sock, 0.: 013 S o d e r q u i s t , J . A . : 066, 465 Solau, D.R.: 067 S o l l a d i e , G.: 436 Sondej, S . C . : 191 Song, Y.H.: 338 S o n n l e i t n e f , B. : 31 8 Sonoda, N. : 058, 077, 092, 097 170, 235, 259, 426 438, 458 Sonoda, T.: 235 Sootome, N.: 266, 276 S o r g i , K.L.: 069 S o r i a , J.J.: 422 S o t e l o , 0.: 408

INDEX

Souppe, J.: 024, 307 Spadaro, A. : 006 S p a g o l o , P.: 380 S p d l t e n s t e i n , 8 . : 374 Spangler, C.W. : 359 S p a t o l a , A.F. : ,021 Speckamp, W.N. : 102, 371, 373 Speranza, G. : 233 Spessard, G.O.: 150 S p i l l a n e , W.J.: 112 Spina, K.P.: 237 S p l e t z e r , E.G.: 291 S p r i n g e r , J.P.: 292, 413, 442 Srebnik, M. : 427 S r i d h a r a n , V.: 362 S r i n i v a s a n , P . S . : 017 S r i v a s t a v a , P.C.: 453 S t a a b , E.: 328 S t a b l e r , R.S.: 422 S t a d l w i e s e r , J. : 428 Stakem, FIG.: 387 S t m , H. : $95, 370 StmOS, I . K I : 398 Stang, P.J. : 281 S t a n t o n , S . A . : 437 S t a r k , S.R.: 447 S t a r n e r , W.E.: 1 1 4 Stavinoha, J I L . : 11 9 Steckhan, E . : 457 S t e e l e , J.: 292 S t e e l e , R.W.: 366 Stegenga, S.: 373 Stehouwer, P.M.: 249 SteinbachI R . : 024, 025, 332 S t e l a , L. :*358 S t e l i o u , K. : 063, 172 Stephens, C . J . : 383 S t e r c h o , Y.P.: 027 S t e r n b e r g , E.Q.: 486 Stevens, R.V. : 125, 369, 461 Stevenson, T.: 089 S t i l l , B. : S t i l l , W.C .'q3308, 309, 41 1 S t i l l e , J . K . : 059, 060, 074 S t i l l e , J.R.:

085, 262, 419, 472 207

INDEX

AUTHORS

S t o d d a r t , J.F.: 037 S t o e s s e l , S.J.: 419 S t o l l , A.T.: 206 Stone, W.B. : 188 S t o r k , G. : 084, 162, 436 S t r i j t v e e n , B.: 323 Stroud, S.G.: 050, 138 Strvchkov, Y.T.: 478 Stucky, G.: 045 Stufflebeme, G.: 094 S t u l t s , J.S.: 444 Siisse, M a :,409 Suarez, E. : 182 Subramanian, L.R. 080 Suda, T.: 211 Suemitsu, R.: 114, 229 Suemune, H.: 460 Sugahara, S.: 282 Sugasawa, T.: 024, 335 Sugawara, T.: 063, 092, 095

*:

2 90

Sugimura, H.4 442 Suginome, H. : 159, 174, 490 S u g i t a , N.: 156 Sugiura, T.: 474, 491 Sugiura, Y.: 042, 342, 348 Suguira, T.: 421 Sugujama, T.: 071 S u i t s , J.Z,: 481 Sukata, K. : 245 Sulmon, P.: 130 S u l t q o v , R.M.: 034, 083 Sumiya, R.: 309 Sumiya, T.: 034, 172, 228 Sundeen, J.: 471 Sur, M.: 055 Surya Prakash, G.K.: 175, 244

302

Suta, L.R.: 350 S u t l e r , M.4.: 318 Suzuki, A. : 063, 076, 265

290, 354, 455 457, 490

Suzuki, H.

527

* : 079,

080, 122

133, 135, 167 189, 190, 195 201, 204, 213 243, 244, 262 270, 333, 41 1 421, 481, 484 Suzuki, K.4 038, 113, 144, 310 Suzuki, N. 248 Suzuki, S . * l 360, 426, 482 Suzuki, Y . : 315, 343 Sviridov, A.F.: 218 S w a d , K . : 419 Swain, C . J . : 219 Swanson, E.D.: 478 Swanson, R.: 119 Sweeney, J.B.: 424 Swindell, C.S. : 068, 071

-

Sychkova, L.;.: 141 Szarek, W.A, : 298 Taber, D.F. : 346, 403 Tabuchi, T. : 199, 251, 331

344, 395

Taddei, M.: 313, 315 r a g a s h i r a , M.: 349 'Tagliavini, E.: 319, 349 Tajima, K . : 008 Tajima, M.: 239 Taka-Oka, $.: 333 Takagi, K . : 834 Takahashi, K . : 009, 058, 351

358, 417, 474, 480

Takahashi, M.: 213 Takahashi, S.: 410 Takahashi, T. : 126 Takahashi# Y.: 075 Takai, K. : 052, 159, 266, 284

328, 341, 324, 343 347, 349, 357, 358 458, 476 Takaoka, K.: 133, 204 Takase, K. : 253 Takayanagi H.: 007 Takechi, K;*: 189 Takeda, A. : 304 Takeda, M.:

120

528

INDM

AUTHSS

Tani, K.*: 389 Takeda, T4*: 246, 327, 433 Tanigawa, Y. : 389 Takei, H. : 442 Taniguchi, H.: 070, 342 Takemasa, T.: 010 Taniguchi, N. : 142 Takemoto, Y.: 337 Takeshita, K.: 077 Tanimoto, Y. : 037 Tapia, R.: 274. Takeuchi, R.: 060, 111, 135 Tarbin, J.A.: 274, 275 391, 396 Takeuchi, S. : 079 Tardella, P.A.: 368 Takeyama, J . : 326, 331 Tardivel, R.: 448 Tarhouni, %.: 168 Takido, T. :,242 T a s s i , D.: 315 Takimto, S. : 141 Tata, C.: 424 Takinami, S. : 457 Tatsmi, T.: 212 Takitoh, N.: 104 Tatsuno, T.: 428 Takujama, N.: 042 Tatsuno, Y. : 389 Tamada, M. : 460 Taufet-Kn6pfel , I. : 320 Tamano, MI: 079 Taufer, I.: 150 Tamao, K. : 027, 033, 205 Tavel, G.: 459 309, 337 Tawarayaqa, Y. : 342 Tamarkin, D.: 261 Taya, K. : 300 TamWu, Y.: 100, 207, 210, 220 Tayano, T.: 354 364, 367, 394, 398 400, 408 Taylor, B.S. : 075 Tamaru, Y.: 428, 471 Taylor, D . A . i 434 Tamblyn, W.H. : 019, 039, 095 Taylor, E.C. :,247, 393 Taylor, R.J.$. : 424, 490 * 352 Taylor, R.T. : 043, 158 Tamborski, C . : 074 Teach, E.G.: 366 T a m , C . : 323 Tenge, B. J. : 374 Tamura, 0 . : 397 Terada, T.: 311 Tamura, R.4 412 Teranishi, S. : 027, 211 Tamura, R. 270, 388, 437 Terao, K.: 102, 365 Tamura, Y.*i 159, 336, 397 Terao, Y.: 1 1 3 Tan, R.P.K.: 359 Terashima, M. 127, 375, 388 an, T.s.: 030 Terashima, S.": 315, 343 Tanabe, M.: 229 Terpinski, J.: 190 Tanate, Y.: 407 Teshima, N.: 203 Tanaka, H.: 013, 072, 233 Teshirogi, J. :,098 285, 342 Tanaka, K.*. 085, 130, 367, 422 Testaferri, L. : 121 Texier-Mullet, F. I 096 Tanaka, M . * i 230, 378, 409 Teyssie, P,: 093 Tanaka, N.: 125 Tezuka, T. : 176 Tanaka, S. : 181 , 393 Thebtaranonth, C . : 257 Tanaka, T.: 205, 307, 309 Thebtaranonth, Y. : 257 Tanaka, Y.: 248, 439 Thianpatanagul, S.: 362 Tanguay, G.: 013, 221 Thiebault, H.: 448 Tani, H.: 079, 195 Thiensathit, S.: 476

-

INDEX

AUTHORS

Thomas, A . P . : 070

Thomas, D.G.: 1 1 4 Thomas, S.E. : 171, 262

Thompson, D.W. : 346, 427 Thompson, P.A.4 161, 342 Thompson, W.J. : 405 Thomsen, I.: 102 Thorat, M . : 409 Thurkauf, 8 . : 324 Tiecco, M. : 171 Tingoli, M. ,071, 171 Tinucci, LI: 313 T i u s , M . A . : 324 Tobito, Y.: 448 Toder, B.H.: 416 Toki, T.: 426 Tokitoh, N. : 122, 386 Tokles, M . : 309 Tolstikov, C.A.4 276 Tomaselli, G.A. : 463 Tomasini , C. : 332 Tcmimori , K . : 320 Tominaga, H.: 212 Tomino, I. :,037 Tcmioka, H. : 214, 456 Tomioka, K . : 463 Tmita, K.: 331, 389, 451 Toofan, J.: 053, 056, 214 Tor, Y.: i91 Torii, S. : 013, 062, 072 219, 233, 237 285, 299, 342 341, 345, 440 Torreilles, E. : 056 Torres, C. : 274 Torssell, K.B.C. : 468 Tortajada, J.: 061 Toru, T. : 399 Toshida, Y . : OQ? Toshimitsu, A. 102, 365 TotZauer, W.: 232 TOUT, J.M.: 006, 407, 474 Toussaint, 0.: 195, 208 Toyoda, H. : 044 Toyoda, M. : 062 Trave, S. : 060

,

.

Traynham, J.E.*: 190 Trimble, L.A.4 296

529

Trimitsis, C. : 224 T r i u z , A.: 483 Trivedi, C.K, : 347 Trombini, C2 : 319, 349 Trost, B.M. ; 083, 098, 210 268, 270, 286 290, 392, 412 413, 420, 441 445, 468, 469 Troupe1 , M. : 01 3, 260 Troyansky, E.I.: 464 Trudell, M.L.: 095 Tsai, D . J . S . : 346 Tsai, Y.-M.: 373 Tseng, C . C . i 070 Tseng, C.K. i 366 Tsien, Y.-L. : 268 T s u b a k i , K.: 408 Tsubata, K.: 111 Tsuboi, Ta. : 056 T s u b i , Ts.: 056 Tsubniwa, N.: 334, 345 Tsuchida, T. : 3 i 7 Tsuchihasbi , C. : 038 Tsuda, T. : 477 Tsuge, S.: 051 Tsugoshi ,,T. : 1 29 T s u j i , J. : 007, 078, 117 151, 195, 212 223, 228, 232 387, 405, 417 418, 421, 466 472, 474, 478 479, 483, 491 Tsuji, M.: 270 T s u j i , Y . : 060, 101, 105, 111 135, 391 , 396 Tsujimoto, K.: 327 Tsukahara, Y.: 488 Tsukamoto, M. : 393 Tsukanaka, T. : 248 Tsukihara, K . : 056 Tsmaki, H.: 332 Tsunekawa. H.: 425

530

Tsmo, Y.: 188 Tilclanantel , W. : 251 Tucker, J . R . i 093 Turner, J. V. * : 329 Tustin, G.C. : 155 Twohig, M.F.: 228 Uang, B.J.: 430 Uchida, K.: 103 Uchida, Y.: 212 Uchikawa, M.: 313 Uchiyama, K.: 273 Uchiyama, M.: 329 Ueda, K . i 062 Ueda, M. : 098, 099, 273 Ueda, W.: 410 Uehara, S . i 460 Uemura, S. : 102, 181, 260 365, 447 Ueno, K . 4 460 Ueno, Y . : 144, 196, 211 272, 345, 448 Uggeri F.: 015, 451 Ugi, IT*:,105, 242 Uguen, I). : 155 Ukai, J.: 254, 433 Ukaji, Y.: 315, 322 Ukita, T.: 212, $67, 359 Umani-Ronchi, A. : 135, 319, 349 Umei, Y.: Oz8 Umemoto, T. : 331, 451 Uneyama, K.: 062, 219, 344, 345 Uno, H. : 484 Uno, M.: 410 Urch, C . J . : 092 Urpi, F.: 099, 104 Urz, R.: 474 ushio, Y.:

INDEX

AUTHORS

020

Utaka, M. : $04 Utimoto, K . : 263, 283, 328 349, 422, 458 Uyaya, S.: 237 Vagberg, J.: 416 Vaccaro, W. : 361 Valderrama,, J.A.: 274 Vallee, D. : 363 Valoti, E.: 313

Van Chiem, P.: g16 Van der Gen, A. : 436 Van Hemelryck, B,: 061 Van Leusen, A.M. : 061, 471 Van Schaik, T. A.M. : 436 Van Schnering, H.-G.: 146 Vanderesse, R. : 082 Vankar, P. : 238 Vankar, P.S.4 160 Vankar, Y .D. 031, 339, 456 Varie, D.L.: i 4 4 Varma, M.: 235 Vam, R.K.: 115 V m a , R.S.: 233, 235, 432 Varney, Y . D . $05 Varvoglis, A. 156 Vatele, J.-M.*i 410 Vaughn, G.D.: 441 Vaultier, M . : 130, 133 Vavilikolanu, P.R.: 238 Vawter, E.J.: 091 Vedejs, E. : 153, 219, 444 Vederas, 3.C. : 296, 364 Veenstra, S.JI: 044 Venanzi, L.M. i 120 Venturello. C . : 176 Verhe, R.: 381 Verlhac, J9-B.: 384, 460 Vermeer, P.*': 249, 438 Vernon, P.: 379 Vessal, B.: 054 Viala, J.: 349 *. Viallefont, Ph. 363, 376, 378 V i d a l , Y.: 215 Viehe, H.G. : 368 Vijayaraghavan, S.T.: 408 Vilapiana, M.3.: 034 Vilarrasa, J. : 099 Villa, C.A. : 475 Villacorta, Q.M. : 146 Villernin, D. 096, 485 Villieras, J. : 168, 420 Vincenti, M.: 304 Viout, P.: 269 Vishwakarma, L.C. : 333 Viswanathan, M.: 075

-

-

.

INDEX

AUTHORS

Vitagliano, A!: 343 VO Q W g , L.: 353 Vo Quang, Y.: 353 Vogel, D.E. : 4x4 Volhann, R.A. : 579 Vollhardt, K.PZC. : 067, 486 Vorbriiggen, H. : 117 Voronkvo, M.G. : 01 6 VOW,

015 Vostrikova, O.S.: 034, 083 Vukicevic, R.: 056 Wtilchli, R.: 109 Wachi, M.: 211 Wada, F. : 078 Wada, M.: 286, 345, 369 Wade, A. R. :,061 Wadia, M.S. : 241 Wakabayashi, S.: 235, 344

G.:

Wakabayashi, Y.: 341 Wakamatsu, K.: 208, 251, 345 Wakamatsu, T.: 363 Wakamoto, K.: 3fi Walbrsky, H.M.

: 237

Waldmann, H . 4 017 Walker, B.J. : 005 Walker, J . C . : 227, 293, 306 walkup, R.D.: 322 Wallace, P.: 095 Waltermire, R.E.: 352 Walters, M.A.: 124 Wag, B.L.4 069 Wang, K.K. : 002, 491 Wang, N.: 032 Wang, P.-C.: 165 Wannamaker, M.W.: 270 Wanner, K . P . : 479 Ward, A.D. : 401, 447 Ward, F.E.: 301 Warin, R.: 093 Warner, P.4 163, 293 Warren, S. : 095, 257, 258 Waseda, T.: 288, Wasserman, H.H. : 461 Watanabe, A.: 240 Watanabe, H. : 248, 290

531

Watanabe, K.*:

188, 244, 290 337

Watanabe, Y .*: 001, 060, 101

105, 111, 135 196, 290, 391 396, 423 Waterhouse, J.: 064 Waterson, 258 Watt, D.S. : 231, 310, 330, 405 WattanasiQ, S.: 217 Wayda, A. : 032

p.:

Weatherford 111, W.D.: 165 Webb 11, R.R.: 101 Webb, M.W./ 165 Webb, T.R. : 118 Weber, G.: 108 Weber, R.H. : 318 Weber, T.: $96 Weber, W.P. : 347 Wegner, G. : 088 Weiberth, F.J.: 131 Weigel, L.9. : 317 Weiler, L. : 418 Weinberger, B.: 013, 221 Weingold, D.H.: 019, 039 Weinig, P.: Og5 Weinreb, S.M. : 318, 371, 375 Weiss, R.: 295, 370 Weiss, U.: 120 Weitzer, H . 4 036 Welch, S . C . : 173 Welker, M.E.: 090, 163, 293 Wells, G.J.: 320 Welvart, Z. : 234 Wenderoth, B.: 024, 025, 332

*

3 3'1)

.JJL

Wenkert, E. : 014, 068, 071, 250 Werner, J.A. : $34 Werstiuk, N.H. : 230 Westermann, J.: 024, 025, 079 Westmijze, H.: 249, 438 Wetzel, J.M. :,032 Wheeler, C.J. : 254 Whelm, J.: 423, 443 White, A.W.: 273 White, S.B.: 273

532

AUTHORS

White, W.L.: 401 Whitesell, J . K . : 057, 230 Whitesell, M.A. : 057, 230 Whitney, S.E.: 091 Whittle, R.R.: 375 Wichelhaus, J.: 153 Wickham, G.: 071 Widdowson, .D.A. : 072, 077, 21 6 Widler, L.4 322 Widmer, U . : 141 Wiemer, D.F.*:’ 051. 224 I.!ieschollek, *R. : 254 Wilbur, D.S. : 188 Wilde, H.: 108 Wilde, R.G.: 444 Wilhelm, R.S.: 076, 091, 092

Williams, D.J.4 037 Williams, D.R. : 046, 396, 427 Williams, L.: 433 Williams, R.M. : 298

Willison, D.: 430 Wilson, J.W.: 033 Wilson, J.W.: 264 Wilson, J . Z . : 046 Wilson, K.D.4 372 Wilson, S.R. : 041, 469, 475 Wilson, W.K.: 294 Winstead, R.C.: 427 Wittenberger, S.: 444 Woell, J . B . : 139, 153, 155, 156 Wolf, R.: 457 Wolff, M . : 018 Wollmann, T.A.: 322 Wolsieffer, L.A.: 032 Woltermann, A.: 302 Wong, G.S.K.: 103 Wong, H.: 123 Wong, S.: 002 Wonnacott, A.: 025 Wright, B.T.: 229 Wright, S.W.: 152 Wrobel, J.E.: 030 Wroble, R.R.: 231 WU, P.-L.: $71 Wuest, J.D. : 022 Wulff, G.: 1.53

INDEX

* : 321, 325, * 442, 462 P.G.M. : 161, 342

Wulff, W.D.

Wuts, Wymann, W.E.: Xu, Y.: 380 Xu, Z.: 069 Yahata, Yakura, Yamada, Yamada, Yamada, Yamada, Yamada,

413

113

N.: 058 T.4 336 K . : 120, 216, 395, 490 M.: 478 S.: 159, 174 T.4 246, 309 Y. : 071, 100, 210 220, 337

Yamagata, T.: 389 Yamagata, Y.: 389 Yamagkuchi, MI: 331 Yamaguchi, M. : 030, 147, 199 251, 285, 288 297, 305, 312 313, 344, 395

393

Yamaguchi, R.: 303 Yamaji, T.: g48 Yamakawa, K . : 220, 237, 338

384, 409

Yamakawa, Y.: 423 Yamamoto, A . i 478 YamamOto, H. : 031, 038, 039 096, 129, 283, 326, 433, 485 Yamamoto. J. : 056

*

Yamamoto;

064, 128, 254, 287,

K . 4 007

122 192 284

339

YamamOto, M.*: 395 Yamamoto, T.*: 102 Yamamoto, Y . : 075, 092, 210 213, 318, 343 369, 391, 396 Yamamura, K. 433, 484 Yamamura, Y. 129 Yamana, Y.: 07, 157 Yamanaka. Y . 3 42 Yamanoi, T.: 036, 037, 318, 330

INDEX

AUTHrnS

Yamasaki, H.: 144 Yamasaki , Y. :,058 Yamashita, A.,: 205

Yamashita, J. 070, 201, 255 Yamashita, M.*I 114, 184, 229 Yamashita, S.: 285, 342 Yamashita, T.: 128 Yamashita, Y.: 072 Yamato, T.: i75 Yamauchi, T. : 014 Yamawaki, K.: 211

Yamazaki, N.: 036 Yamazaki, S.: 315 Yamazaki, Y.: 239, 366 Yanagi, K.: 400 Yanagi, T.: 003 Yanagihara, N.: 422 Yanai, T.: 180 Yang, D.C.: 325, 413 Yangs J.: 359 Yang, s.: 200 Yang, T.-K.: 114 Yang, Y.-L.: 439

Yang, z-Y.: 001 Yao, K.: 221 Yashunsky, D.V.: 218 Yasuda, H.4 232, 397 Yasuda, M. : 128

Yasmura, M.: 052

Yasunaga, H.: 047, 461 Yatagai, H.: 343 Yates, S.W.: 165 Yates, K.: 168

Yen, S.-J.: 070 Yevich, J.P.: 131

Y i , K.Y.: 136 Y i , Q.: 244 Y i j u n , C.:,365 Yoakim, C . : 029, 046, 048 Yoda, H. : 422 Yogo, T. : 063 Yokoo, K.: 342 Yokoyama, M.: 084, 183, 326

342

Yokoyama, S.: 045 Yokoyama, T.:

093

533

Yokoyama, Y.: 075 Yon, G.H. :,086 Yoneda, F. : 085 Yoneda, R . 4 482 Yoneda, S. : 302

Yonemitsu,,O.: 014 Yoon, 'N.M. : 022, 051 Yoon, V.C.:,119 Yoshida, Yoshida, Yoshida, Yoshida,

J. : 268, 492, 445

S.: 239, 243 T. 065, 211

105, 243 100, 207, 260 220, 364, 367 394, 398, 400 ,408, 428, 471 Yoshikawa, S. : 144

Y.'. Yoshida, Z.*I

Yoshi kawa, T. :,120 Yoshikoshi, A. : 303

Yoshimura, N.: 020 Yoshinaga, Y,: 327 Yoshioka, H. : 184 Yoshitake, M.: YOU, M.: 279

395

Youn, I.K.: 086

Young, C.G.4 215 Young, R.N. : 030, 145 Youngdahl , K. : 040 Yu, L.-C.: 432 Yuba, K . : 305 Yue, S. : 362 Yuhara, M.: 483, 491 Yukawa, T.: 440 Y u k i z a k i , H.: 068 YUS, M.: 110, 224, 251, 252

267, 308, 370, 448

Zacharie, B. : 022 Zahalka, H.A.: 035

Zahra, J.-P.: 281 Zakrzewski, J.: 256 Zanirato, P. : 134

Zanirato, V.: 471, 483 Zappi, G.D.4 011 Zard, S.-Z. : 029, 129, 181 Zaugg,

H.E.

*

:

234, 385 112

534

Zefirov, N.S.*: 367 Zelle, R.E.: 295 Zenki, S.: 274 Zezza, C . A . : 116 Zhai, D. : 298 Zhang, S.: 419 Zhang, Y.-A,: 072 Zheng, J.: 412 Ziegler, F.E. : 249 Zinov'eva, L.V. : 067 Zocher, D.H.T. : 399 Zorc, B.: 214 Ziiger, M.F.: 318 Zucker, P&: 475 Zupan, M. :,186, 449 Zweifel, C. i 282, 289 Zwierzak, A. : 113 Zyk, N.V. : 367

AUTHORS

INDEX

Compendium of Organic Synthetic Methods Volume 6

Compendium of Organic Synthetic Methods

Compendium of Organic Synthetic Methods