Tin in Organic Synthesis - Michel Pereyre, Jean-Paul Quintard and Alain Rahm Auth.pdf

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To Professors Raymond Calas and Jacques Valade
who initiated and developed the discipline of
organometallic chemistry at the University of Bordeaux
To Josette and Sabine Pereyre
Suzette, Delphine and Jérôme Quintard
Daniele, Caroline and Benjamin Rahm
whose encouragement, patience and understanding
made this task so much easier
Tin in Organic Synthesis
Michel Pereyre
Jean-Paul Quintard
Alain Rahm
Laboratory of Organic Chemistry, University of Bordeaux
London Boston Durban Singapore Sydney Toronto Wellington
All rights reserved. No part of this publication may be reproduced or transmitted in
any form or by any means, including photocopying and recording, without the
written permission of the copyright holder, application for which should be
addressed to the Publishers. Such written permission must also be obtained before
any part of this publication is stored in a retrieval system of any nature.
This book is sold subject to the Standard Conditions of Sale of Net Books and may
not be re-sold in the UK below the net price given by the Publishers in their current
price list.
First published 1987
© Butterworth & Co. (Publishers) Ltd, 1987
British Library Cataloguing in Publication Data
Pereyre, Michel
Tin in organic synthesis.
1. Organotin compounds
I. Title II. Quintard, Jean-Paul
III. Rahm, Alain
ISBN 0-408-01435-0
Library of Congress Cataloging-in-Publication Data
Pereyre, Michel.
Tin in organic synthesis.
Bibliography: p.
Includes index.
1. Organotin compounds. 2. Chemistry, Organic—
Synthesis. I. Quintard, Jean-Paul. II. Rahm, Alain.
III. Title.
QD412.S7P47 1986
ISBN 0-408-01435-0
Typeset by Scribe Design, Gillingham, Kent
Printed and bound in Great Britain by Anchor Brendon Ltd, Tiptree, Essex
The organic compounds that serve the needs of man are becoming
increasingly sophisticated. One of the great challenges of organic chemistry
is to make such complex organic molecules readily available. Effective
synthetic strategy requires the development of novel selective reactions
and reagents. Organostannane chemistry has been playing an increasingly
important role in serving as a source of new reagents and selective
transformations. Two areas that have been strongly impacted by the
compounds of tin illustrate the potential of organostannanes for synthesis.
Use of organostannanes for generation of carbon radicals for C-H and
C-C bond formation from a wide variety of functional groups has surfaced
as a powerful strategy for synthesis. Alternatively, the C-Sn bond serves as
a nucleophilic reaction centre. Transmetallation reactions also provide a
source of reactive nucleophiles. Exchange of the C-Sn bond for a C-Li
bond represents one of the cleanest ways to generate reactive organo-
lithium reagents - many of which are unavailable by other methods.
Transition metal catalysed reactions have grown in importance owing to
the ability to transfer a carbon from tin to the transition metal.
Tin in Organic Synthesis
is a timely account of the current status of this
area. A practitioner of organic synthesis must be aware of the organic
chemistry of tin. It is no longer satisfactory to think that a knowledge of tin
hydride is all that is required. This systematic presentation of the organic
chemistry of tin will introduce students to this growing field of synthesis.
For the active researcher, this book serves as a rich source to find what
kinds of organostannanes are available, their major reactions, and many
specific examples illustrating their potential. It should also serve to
illustrate the many aspects where our knowledge is limited, and therefore
provide an impetus for new research. Coming from one of the leading
laboratories of organotin chemistry,
Tin in Organic Synthesis
is an
authoritative source for a rapidly expanding field.
Barry M. Trost
Department of Chemistry
University of Wisconsin-Madison
February 1986
Organotin chemistry has undergone a considerable development over
recent decades. A striking point is the strong impetus which has been
given, during the past fifteen years, towards the applications of organotin
compounds as reagents or intermediates in organic synthesis. It is now time
to review the present status of knowledge in that particular area and, along
the way, to point out directions for future developments.
The book has been divided into four parts. Following a brief
introduction to organotin chemistry, synthetic applications involving
tin-hydrogen, tin-carbon and tin-heteroatom bonds are presented. The
index will guide the reader interested in specific types of organic
transformation. Although the book is not intended to be exhaustive,
special emphasis has been given to the more recent findings with a
bibliography including 1984 and part of 1985.
It is a pleasure to acknowledge the contribution of Professor S. David
(Orsay), who constructively commented on the aspects related to
carbohydrate chemistry, and to sincerely thank Professor B.M. Trost
(Madison) who, as a practitioner of tin in organic synthesis, kindly agreed
to write a foreword.
All the members of the 'tin group' of our laboratories, and more
specially Drs C. Cloutour, B. Delmond, B. Jousseaume and B. Maillard,
must be warmly thanked for their help and encouragement at all stages of
this task. Also the preparation of the manuscript would not have been
possible without the patient, skilful and smiling efforts of Mrs E. Breliere
and M.F. Penna.
Finally we express our acknowledgements to Butterworths, who
tolerated our delays and carried out the indispensable linguistic cleaning.
M.P., J.-P.Q., A.R.
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