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Edited by Didier Astruc
Modern Arene Chemistry
2002 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
ISBN: 3-527-30489-4
Modern Arene Chemistry . Edited by Didier Astruc
Copyright
8
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Modern Arene Chemistry
Edited by Didier Astruc
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Editor
9
This book was carefully produced. Nevertheless,
editor, authors and publisher do not warrant the
information contained therein to be free of errors.
Readers are advised to keep in mind that statements,
data, illustrations, procedural details or other items
may inadvertently be inaccurate.
Prof. Didier Astruc
LCOO, UMR CNRS N o 5802
Universit´ Bordeaux I
33405 Talence Cedex
France
Library of Congress Card No.: applied for
A catalogue record for this book is available from the
British Library.
Die Deutsche Bibliothek – CIP Cataloguing-in-
Publication-Data
A catalogue record for this publication is available
from Die Deutsche Bibliothek
2002 Wiley-VCH Verlag GmbH & KGaA,
Weinheim
All rights reserved (including those of translation
in other languages). No part of this book may be
reproduced in any form – by photoprinting,
microfilm, or any other means – nor transmitted or
translated into machine language without written
permission from the publishers. Registered names,
trademarks, etc. used in this book, even when not
specifically marked as such, are not to be considered
unprotected by law.
Printed in the Federal Republic of Germany.
Printed on acid-free paper.
Typesetting Asco Typesetters, Hong Kong
Printing Strauss Offsetdruck GmbH, M¨rlenbach
Bookbinding J. Sch¨ffer GmbH & Co. KG,
Gr¨nstadt
ISBN 3-527-30489-4
(
v
Contents
List of Contributors xvi
Arene Chemistry : From Historical Notes to the State of the Art 1
Didier Astruc
The History of Benzene 1
The History of Aromaticity 5
Some Key Trends Towards Modern Arene Chemistry 9
Aromatic Chemistry: From the 19 th Century Industry to the State of the
Art 11
Organization of the Book and Content 13
References 16
1 The Synthesis of Tris-Annulated Benzenes by Aldol Trimerization of Cyclic
Ketones 20
Margaret M. Boorum and Lawrence T. Scott
Abstract 20
1.1 Introduction 20
1.2 Truxene and Truxone: Venerable Prototypes 21
1.3 Other Examples 23
1.4 Limitations 27
1.4.1 Experimental Observations and a Working Hypothesis 27
1.4.2 Guidance from Calculations 29
1.5 Conclusions 30
References 31
2 Oligounsaturated Five-Membered Carbocycles – Aromatic and Antiaromatic
Compounds in the Same Family 32
Rainer Haag and Armin de Meijere
Abstract 32
2.1 Introduction 32
2.2 Cyclopentadienyl Cations 33
2.3 Fulvene and Spiroannelated Cyclopentadiene Derivatives 37
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