General and synthetic methods, Volume 12

572 Pages·1990·30.37 MB·english

by  G. Pattenden

General and Synthetic Methods
Volume 12

A Specialist Periodical Report
General and Synthetic
Methods
Volume 12
A Review of the Literature Published in 1987
Senior Reporter
G. Pattenden, Department of Chemistry, University of Nottingham
Reporters
K. Cooper, Pfizer Central Research, Sandwich,
D. J. Coveney, University of Nottingham
T. Iu. Dank, University of Warwick
C. W. Ellwood, University of Nottingha
T. Gallagher, University of Bath
D. C. Harrowen, University of Notting
D. W, Knight, University of Nottingham
T. V. Lee, University of Bristol
K. E. 8. Parks, Roche Products Limited, Welwyn Garden City,
Herts.
G. M. Robertson, Glaxo Group Research, Ware, Herts.
N. Simpkins, Queen Mary College, University of London
S. E. Thomas, University of Warwick
C. J. Urch, lCl Agrochemicals, Bracknell, Berks.
P. J. Whittle, Pfizer Central Research, Sandwich, Kent
SOCIETY OF
HE MISTRY
ISBN 0-85 186-934-3
ISSN 0141-2140
Copyright 0 1990
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 inf ormation storage and retrieval systems-without written
permission from The Royal Society of Chemistry
Published by The Royal Society of Chemistry,
Thomas Graham House, The Science Park, Cambridge CB4 4WF
Printed and bound in Great Britain by
Bookcraft (Bath) Ltd
Introduction
This report covers the period January to December 1987. The broad
aims of our survey of 'General and Synthetic Methods' remain as set
out in last year's Report. We welcome a number of new contributors
to Volume 12 which has an identical layout to that followed in
Volume 11. As always, comments and suggestions from our readership
regarding the coverage and format of this Report are very helpful.
March 1990 G. Pattenden

Cont en ts
Chapter 1 Saturated and Unsaturated Hydrocarbons 1
By N. Simpkins
1 Saturated Hydrocarbons 1
2 Olefinic Hydrocarbons 1
3 Conjugated l13-Dienes and
Non-conjugated Dienes 14
4 Allenes 19
5 Alkynes 25
6 Enynes and Dlynes 27
7 Polyenes 32
References 32
Chapter 2 Aldehydes and Ketones 37
By K.E.B. Parkes
1 Synthesis of Aldehydes and Ketones 37
Oxidative Methods 37
Reductive Methods 40
Methods Involving Umpolung 44
Other Methods 45
Cyclic Methods 49
2 Synthesis of Functionalised Aldehydes
and Ketones 58
Unsaturated Aldehydes and Ketones 58
a-Substituted Aldehydes and Ketones 63
Dicarbonyl Compounds 68
3 Protection and Deprotection of Aldehydes
and Ketones 72
4 Reactions of Aldehydes and Ketones 75
Aldol and Other Reactions of Enolates 75
Conjugate Addition Reactions 78
References 84
...
Vlll Contents
Chapter 3 Carboxylic Acids and Derivatives 91
By D.W Knight
1 Carboxylic Acids 91
General Synthesis 91
Anhydrides 93
Diacids 93
Diacid Half Esters 93
Hydroxy-acids 95
Keto-acids 98
Unsaturated Acids 98
Aromatic Acids and Esters 101
Arylacetic Acids and Esters 101
Carboxylic Acid Protection 102
2 Carboxylic Acid esters 104
Esterification 104
General Synthesis of Esters,
Thioesters, Dithioesters, and
Selenoesters 105
Diesters 112
Hydroxy-esters 115
Keto-esters 124
Unsaturated Esters 132
3 Lactones 142
Butyrolactones 142
a-Methylenebutyrolactones 151
Butenolides 153
Phthalides 155
Tetronic Acids 157
Valerolactones 159
Macrolides 162
4 Carboxylic Acid Amides 165
Amide Bond Formation 165
React ions 167
5 Amino-acids 170
a-Amino-acids 170
f3-Amino-acids 177
Y and Other Amino-acids 179
Asymmetric Hydrogenation of
Unsaturated Amino-acid Derivatives 181
Amino-acid Protection 182
References 186