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Book Review Modern Arene Chemistry. Edited by Didier Astruc

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reagents has contributed enormously to
the armory of synthetic organic chemistry, and these developments are well
reflected in this latest Houben-Weyl
volume. The excellent graphics enable
one to quickly grasp the essentials of
even the most complex syntheses. In
most cases the alternative methods are
presented alongside each other, which is
a great advantage when working out a
synthetic strategy. On the other hand,
the volume is less suitable as a work of
reference for standard preparations of
particular organosilicon compounds,
since finding the required information
is often laborious or even fails completely. Better sources are available for
this purpose.
The technical quality of the volume
is excellent and the text is almost free of
errors. However, this reviewer has had
to accept that his name was spelled
correctly four times but incorrectly five
Hubert Schmidbaur
Anorganisch-Chemisches Institut
Technische Universit‰t M¸nchen
Modern Arene Chemistry.
Edited by Didier
Astruc. Wiley-VCH,
Weinheim 2002.
617 pp., hardcover
E 169.00.–ISBN
About 150 years ago Perkin, through his
transformations of anilines and other
aromatic compounds, brought more color into our daily lives. Are there still new
developments in such a traditional area
of chemistry? In this book you will meet
some of them!
The monograph deals with modern
transformations of arenes and with the
properties of delocalized p systems in
the materials sciences. Therefore only
part of the literature is covered. Didier
Astruc has organized numerous wellknown scientists in their respective
fields into writing contributions and
reviewing the advances of the past two
decades. From the arrangement of the
16 individual chapters it is difficult to
find a unifying concept that has guided
the book.
After a short but very interesting
introduction to the history of aromatic
compounds, the first contribution reports on the aldol trimerization of cyclic
ketones yielding symmetric benzenes.
The following chapter discusses multiply
unsaturated polycyclic structures, including aromatic and mainly anti-aromatic systems. The next two reviews
focus on palladium-catalyzed arylation.
First, A. Suzuki summarizes the reaction
which is named after him, providing a
complete survey which is structured
according to the substrates used. The
examples in natural product synthesis
are well chosen and underline the potential of this coupling methodology.
Unfortunately, the closely related Stille
and Kumada-Negishi cross-coupling reactions are not covered by this book!
The contribution about the arylation of
amines is well done, but is already
available elsewhere in similar versions
by the same author (J. F. Hartwig) or by
S. L. Buchwald in other recent monographs. The following short and condensed discourse deals with new methods for the synthesis of aromatic compounds starting with triple bonds. Two
subsequent chapters deal with acetylene-bridged aromatic systems. The contributions by F. Diederich and H. F.
Bunz lead to applications in materials
science. Four chapters on metal-arene
compounds form a significant part of the
book. The sequence of the individual
chapters is interrupted by a state-of-theart contribution about directed orthometalation. The section on metal-arene
complexes starts with the Dˆtz reaction,
reviewed by the inventor himself. A
discourse about osmium- and rheniummediated selective dearomatization
comes next. A review of nucleophilic
substitution in chromium-arene complexes is followed by a chapter dealing
with analogous reactions of cyclopentadienyliron complexes. Chapter 13 is
¹ 2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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devoted to the effects of charge transfer
on the structure and reactivity of aromatic systems. Since that particular discourse forms the basis for a deeper
understanding of many other contributions, it should have been placed earlier
in the monograph. The following two
reviews deal with the oxidative conversion of aromatic systems, the first of
these covering the oxidative biaryl coupling reaction and the second the related
transformation of phenols into the corresponding quinols and quinol ethers.
The book finishes with a chapter about
supramolecular switches or machines
based on rotaxanes, in which the aromatic systems serve as a device which
features a specific p ± p interaction. This
survey can be found in a similar form in
other monographs.
The individual chapters are complete and well structured. Most contributions have a textbook style. Although
the book cannot cover all topics, it is
unfortunate that some important methods for the synthesis of aromatic systems, such as the Boger reaction, are
The book has been carefully produced. However, the graphical style of
the structural formulas is not uniform in
all the chapters. The incidence of typos
in the written part and the schemes is at
a tolerable level, but sometimes there
are differences in bond angles and
spacing (e.g., p. 95) or the captions are
missing (p. 266). The six p electrons of
the benzene rings are often depicted as
circles in the corresponding hexagons.
Unfortunately, this way of presentation
is also wrongly used for polycyclic condensed aromatic systems.
In summary, the monograph provides an excellent overview of some
recent developments in modern arene
chemistry. In the topics covered, the
book fills in the gaps left by previous
reviews in the literature, and it will
definitely be compulsory reading for
chemists working in these areas. Despite
some small weak points this valuable
book will have its place in every good
library collection.
Siegfried R. Waldvogel
Organisch-Chemisches Institut
Universit‰t M¸nster (Germany)
Angew. Chem. Int. Ed. 2003, 42, No. 7
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