Modern arene chemistry - Astruc, Chemia
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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
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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