Table Of Content

General and Synthetic Methods Volume 6 A Specialist Periodical Report General and Synthetic Methods Volume 6 A Review of the Literature Published during 1981 Senior Reporter G. Pattenden, Department of Chemistry, University of Nottingham Reporters R. C. Brown, Fisons p.l.c., Loughborough, Leicestershire J. M. Clough, I.C.I. Plant Protection Division, Bracknell S. C. Eyley, Fisons p.l.c., Loughborough, Leicestershire P. F. Gordon, I.C.1, Organics Division, Manchester P. R. Jenkins, University of Leicester A. P. Johnson, University ofleeds R. C. F. Jones, University of Nottingham G. Kneen, Wellcome Research Laboratories, Beckenhem, 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 G. M. Robertson, University of Nottingham The Royal Society of Chemistry Burlington House, London, WIV OBN ISBN 0-85 186-874-6 ISSN 0141-2140 Copyright @ 1983 The Royal Society of Chemistry AN Rights Reserved No part of this book may be reproduced or transmitted in any form or by 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 Introduction This sixth Report on General and Synthetic Methods covers the literature from January to December 1981. The presentation of most data is similar in scope and format to the previous volumes in the series, with the exception that a new chapter ‘Highlights in Total Synthesis of Natural Products’ replaces the earlier title ‘Strategy and Design in Synthesis’. Dr. Knight, one of only two remaining members of the original team of contributors to the Reports, provides his last contribution in Volume 6, and I thank him for his enthusiastic collaboration over the past six years. December 1982 G. PATTENDEN V Contents Chapter 1 Saturated and Unsaturated Hydrocarbons 1 By J. M. Clough 1 Saturated Hydrocarbons 1 2 Olefinic Hydrocarbons 5 3 Conjugated 1,3-Dienes 38 4 Non-conjugated Dienes 44 5 Allenic Hydrocarbons 11 6 Acetylenic Hydrocarbons 47 7 Enynes and Diynes 50 8 Polyenes 52 Chapter 2 Aldehydes and Ketones 56 By S. C. Eyley 1 Synthesis of Aldehydes and Ketones 56 Oxidative Methods 56 Reductive Methods 58 Methods Involving Umpolung 61 Other Methods 63 Cyclic Ketones 67 2 Synthesis of Functionalized Aldehydes and Ketones 72 Unsaturated Aldehydes and Ketones 72 a-Substituted Aldehydes and Ketones 80 Dicarbony l Compounds 85 3 Protection and Deprotection of Aldehydes and Ketones 88 4 Reactions of Aldehydes and Ketones 89 Reactions of Enolates and Enolate Equivalents 89 Aldol Reactions 92 Conjugate Addition Reactions 95 Chapter 3 Carboxylic Acids and Derivatives 98 By P. R. Jenkins 1 Carboxylic Acids 98 General Synthesis 101 vii ... Vlll Con ten ts Diacids 102 H ydrox y -acids 103 Keto-acids 104 Unsaturated Acids 104 Decarboxylation 107 Protection and Deprotection 108 2 Esters 109 Esterification 109 General Synthesis and Reactions 109 Dies ters 111 Hydroxy-esters 114 Keto-esters 116 Unsaturated Esters 118 Thioesters 123 Vinylogous Esters 123 3 Lactones 124 General Synthesis 124 @Lactones 125 Butyrolactones 126 Butenolides 133 Phthalides 136 Tetronic Acids 137 a-Meth ylenebutyrolactones 137 Valerolactones 139 4 Macrolides 140 5 Carboxylic Acid Amines 142 Synthesis 143 Macrocyclic Lactams 143 Reactions 143 6 Amino-acids 144 Synthesis 144 Unsaturated a-Amino-acids 147 Asymmetric Hydrogenation 147 Protection and Deprotection 150 Peptide Synthesis 151 Chapter 4 Alcohols, Halogeno-compounds, and Ethers 154 By R. C. F. Jones 1 Alcohols 154 Preparation 154 Carbonyl Group Reduction 157