General And Synthetic Methods

General and Synthetic Methods Volume 8 A Specialist Periodical Report General and Synthetic Methods Volume 8 A Review of the Literature Published during 1983 Senior Reporter G. Pattenden, Deparfment of Chemistry, University of Nottingharn Reporters J. M. Clough, ICI Plant Protection Division, Jealott3 MIA Berkshire K. Cooper, Hizer Central Research, Sandwich, Kent S. G. Davies, University of Oxford S. C. Eyley, Fisons p.l.c., Loughborough, Leicestershire C. R. A. Godfrey, lCl Plant Protection, Jealott's Hi14 Berksbire P. F. Gordon, lCl Organics Division, Mancbester L. M. Harwood, University of Oxford D. W. Knight, University of Nottingham T. W. Lee, University of Bristol S. G. Lister, Wellcome Research Laboratories, Beckenham, Kent K. E. B. Parkes, University of Nottingham G. M. Robertson, University of Nottingham S. E. Thomas, University of Oxford P. Whittle, Pfizer Central Research, Sandwich, Kent The Royal Society of Chemistry Burlington House, London WIV OBN ISBN 0-85186-894-0 ISSN 0141-2140 Copyright 01986 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 Printed in Great Britain by Adlard & Son Ltd, Dorking Introduction This report on General and Synthetic Methods covers the literature published between January and December 1983. The aim of the Reports has been to provide a summary and assessment of reactions and methods in organic chemistry which are new (or useful variants of existing ones) and appear sufficiently general to be useful in synthesis. Interconversions between all the major functional groups are covered in five chapters (Chapters 1-5), and the applications of organometallic compounds in synthesis are treated in Chapter 6, Two further chapters deal with developments in the synthesis of saturated carbocycles (Chapter 7) and saturated heterocycles (Chapter 8) and the final chapter provides a summary of ‘Highlights in Total Synthesis of Natural Products’. A list of reviews on General and Synthetic Methods is collected at the end of the Report. Future volumes in this series will be produced from camera-ready copy of manuscripts. July 1985 G. PATTENDEN Contents Chapter 1 Saturated and Unsaturated Hydrocarbons By J. M. Clough and C. R. A. Godfrey 1 2 3 4 5 6 7 8 Saturated Hydrocarbons Olefinic Hydrocarbons Conjugated 1,3-Dienes Non-conjugated Dienes Allenic Hydrocarbons Acetylenic Hydrocarbons Enynes and Diynes Polyenes Chapter 2 Aldehydes and Ketones By S. C. Eyley 1 Synthesis of Aldehydes and Ketones Oxidative Methods Reductive Methods Methods Involving Umpolung Other Methods Cyclic Ketones 1 1 6 57 65 69 72 75 79 84 84 84 87 89 93 98 2 Synthesis of Functionalized Aldehydes and Ketones Unsaturated Aldehydes and Ketones a-Substituted Aldehydes and Ketones Dicarbonyl Compounds 02 102 109 117 3 Protection and Deprotection of Aldehydes and Ketones 120 4 Reactions of Aldehydes and Ketones Reactions of Enolates Aldol Reactions Conjugate Addition Reactions 123 123 126 128 Chapter 3 Carboxylic Acids and Derivatives By D. W. Knight 1 Carboxylic Acids General Synthesis Acid Chlorides and Anhydrides 131 131 131 134 ... Contents <