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A Specialist Periodical Report General and Synthetic Methods Volume 1 A Review of the Literature Published during 1976 Senior Reporter G . Pattenden, Department of Chemistry, University of Nottingham Reporters N. F. Elmore, I.C.I. Pharmaceuticals, Macclesfield, Cheshire R. C. F. Jones, University of Nottingham D. W. Knight, University College, Cardiff M. Mellor, University of Nottingham S. M. Roberts, University of Salford J. C. Saunders, Lilly Research Centre Ltd., Windlesham, Surrey E. F. V. Scriven, University of Salford K. Smith, University College, Swansea B. P. Swann, Lilly Research Centre Ltd., Windlesham, Surrey D. J. Thompson, I.C.I. Corporate Laboratory, Runcorn, Cheshire D. E. Tupper, Lilly Research Centre Ltd., Windlesham, Surrey S. Turner, Reckitt and Coleman Ltd., Hull The Chemical Society Burlington House, London W I V O B N British Library Cataloguing in Publication Data General and synthetic methods. Vol. 1 .- (Chemical Society. Specialist periodical reports). 1. Chemistry, Organic-Synthesis I . Pattenden, G 547’.2 QD262 ISBN 0-85 184-900-9 ISSN 0141-2140 Copyright 0 1978 The Chemical Society 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 wrilten permission from The Chemical Society Printed in Great Britain by Billings & Sons Limited Guildford and London Introduction The basic aim of this new series of Reports is to provide an up-to-date coverage and appraisal of functional group transformations and methodology in organic synthesis published each calendar year, beginning January 1976. Although the Report will be of interest to all organic chemists engaged in preparative organic chemistry, it will be designed largely for those planning syntheses who are looking for up-to-date general methods and synthetic methodology. As far as possible, every effort will be made to include all reactions and methods which are new, appear synthetically useful, and are reasonably general. An encyclopaedic presentation will be avoided and, within reason, most entries will be accompanied by chemical structures, to aid readers in rapidly scanning the volume. This first volume of ‘General and Synthetic Methods’ is divided into ten chapters. The first five chapters cover all the possible interconversions between the major functional groups, whilst Chapter 6 reports specifically on the applications of organometallic compounds in synthesis. Two other chapters (Chapters 7 and 8) deal with developments in syntheses of saturated, and partially unsaturated, carbocyclic and heterocyclic rings. In ‘Strategy and Design in Synthesis’ (Chapter 9), the author has been given carte blanche, to identify and highlight trends and developments in the philosophy of strategy and design in organic syntheses. From time to time, we plan to devote space in the Reports to special topics which are undergoing rapid development or growth. In this first volume, for example, an additional chapter (Chapter 10) reports on the important growth area of ‘Phase Transfer and Related Methods’. Because of the enormous volume of review literature dealing with general and synthetic methods, we have sought to provide a service to readers and have compiled a comprehensive list of ‘Reviews on General Synthetic Methods’ at the end of the Report. It is inevitable that in a Report of this nature there will be overlap of material from one Chapter to another. We have taken the view, however, that this is acceptable and even desirable in cases where it makes sections more complete and beneficial to the reader. We welcome any suggestions for improving the coverage or presentation of future Reports in this series. July 1977 G . Pattenden Contents Chapte