General and Synthetic Methods Vol 5

458 Pages·8.291 MB·English

by  G Pattenden

General and Synthetic Methods
Volume 5

A Specialist Periodical Report
General and Synthetic Methods
Volume 5
A Review of the Literature Published during 1980
Senior Reporter
G. Pattenden, Department of Chemistry, University of Nottingham
Reporters
A. J. Barker, University of Nottingham
R. C. Brown, Fisons Ltd., Loughborough, Leicestershire
J. M. Clough, I.C.I. Plant Protection Division, Bracknell
K. Cooper, University of Nottingham
S. C. Eyley, Fisons Ltd., Loughborough, Leicestershire
P. F. Gordon, I. C.I. Organics Division, Manchester
A. H. Ingall, Fisons Ltd., Loughborough, Leicestershire
A. P. Johnson, University of Leeds
R. C. F. Jones, Univeristy of Nottingham
G. Kneen, Wellcome Research Laboratories, Beckenham, Kent
D. W. Knight, University of Nottingham
S. V. Ley, Imperial College, London
A. J. Nelson, I.C.I. Organics Division, Manchester
R. A. Porter, Imperial College, London
The Royal Society of Chemistry
Burlington House, London, WIV OBN
British Library Cataloguing in Publication Data
General and synthetic methods. - Vol. 5 -
(Specialist periodical report/Royal Society of Chemistry)
1. Chemistry, Organic-Synthesis-Periodicals
I. Royal Society of Chemistry
547'.2'05 QD262
ISBN 0-85 186-864-9
ISSN 0141-2140
Copyright @ 1982
The Royal Society of Chemistry
All rights Reserved
No part of this book may be reproduced or transmitted
in any form or by any means-graphic, electronic,
including photocopying, recording, taping or
information storage and retrieval systems-without
written permission from the Royal Society of Chemistry
Set in Times on Linotron and printed offset by
J. W. Arrowsmith Ltd., Bristol, England
Made in Great Britain
In trod uc tion
This 1980 Report on General and Synthetic Methods is similar in scope and
foremat to the previous volumes in the series.
The broad aim of these Reports is to provide an up-to-date coverage and
appraisal of functional group transformations and methodology in organic syn-
thesis published during each calender year. As far as possible every effort is
made to include all reactions and methods which are new (or useful variants of
existing ones), and at the same time appear synthetically useful and reasonably
general.
The first five chapters of the Report cover all the possible interconvlersions
between the major functional groups, and Chapter 6 reports specifically on the
application of organometallic compounds in synthesis. Two other chapters
(Chapters 7 and 8) deal with developments in the synthesis of saturated and
partially unsaturated (i.e. non-aromatic) carbocyclic and heterocyclic rings, and
the final chapter highlights trends and developments in strategy and design of
synthesis. A list of reviews on General Synthetic Methods is collected at the
end of the Report.
October 1981 G. PATENDEN

Contents
Chapter 1 Saturated and Unsaturated Hydrocarbons 1
By J. M. Clough
1 Saturated Hydrocarbons 1
2 Olefinic Hydrocarbons 8
3 Conjugated 1,3=Dienes 36
4 Non-conjugated Dienes 41
5 Allenic Hydrocarbons 45
6 Acetylenic Hydrocarbons 49
7 Enynes and Diynes 53
8 Polyenes 55
Chapter 2 Aldehydes and Ketones 59
By S. C. Eyley
1 Synthesis of Aldehydes and Ketones 59
Oxidative Methods 59
Reductive Methods 60
Aldehydes from Acid Derivatives 60
Ketones from Acid Equivalents 62
Methods involving Umpolung 62
Other Methods 68
Cyclic Ketones 72
2 Synthesis of Functionalized Aldehydes and Ketones 76
Unsaturated Aldehydes and Ketones 77
a-S ubstituted Aldehydes and Ketones 81
Dicarbonyl Compounds 84
3 Protection and Deprotection of Aldehydes and Ketones 87
vii
...
Vlll General and Synthetic Methods
4 Reactions of Aldehydes and Ketones 88
Reactions of Enolates and Enolate Equivalents 88
Aldol Reactions 95
Conjugate Addition Reactions 98
Chapter 3 Carboxylic Acids and Derivatives 100
By D. W. Knight
1 Carboxylic Acids 100
General Synthesis 100
Diacids 102
H ydroxy -acids 102
Ke to-acids 103
Unsaturated Acids 104
Decarboxy lation 106
Protection and Deprotection 107
2 Lactones 108
General Synthesis 108
P-Lactones 109
Butyrolactones 109
Butenolides 113
Phthalides 115
Tetronic Acids 116
a -Methylenebutyrolactones 116
Valerolactones 118
3 Macrolides 118
4 Esters 120
Esterification 120
General Synthesis 121
Diesters 123
Hydroxy-esters 125
Ke to -esters 127
Unsaturated Esters 130
Thioesters, Selenoesters, and Thioamides 136
5 Carboxylic Acid Amides 138
Synthesis 138
Reactions 139
Amide- and Peptide-Bond Formation 139
6 Amino-acids 141
Synthesis 141
Unsaturated ct -Amino-acids 141
Asymmetric Hydrogenation 143
Protection and Deprotection 145