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This book is an update of the popular 1994 edition
of Hegedus' organometallic digest for synthetic organic
chemists. Literature is now covered through mid-1999.
Considering the rapid expansion of the use of organometallic reagents
in synthesis during the past five years, such a revision is
very timely. It is difficult to find another text that has the
superb qualities of the Hegedus volume--in particular, its appeal
to practitioners of the art of organic synthesis in industry
and academe, and its breadth, which makes it particularly
suitable as a textbook for an advanced undergraduate course in
organometallic chemistry or an introductory level graduate course
in synthetic applications of transition metal chemistry.
Experts who are looking for detailed discussions of
organometallic reaction mechanisms or subtleties of transition metal
coordination chemistry will be disappointed, however, since
the book is mainly written as an overview of the basic
reaction principles.
Several hundred new references have been added
in the second edition, and several chapters have been
revised. While the discussions of formalisms and mechanisms
and much of hydrogenation (Chapters 1-3) remained
unchanged, Chapter 4, on the chemistry of sigma-alkyl metal complexes,
has been expanded. This chapter comprises some of the
favorites of current synthetic organic methodology such as the
Heck, Stille, and Suzuki couplings. Surprisingly, Pd- and
Ni-mediated aniline and aryl ether formations, which have become
extremely popular in industrial research labs are still conspicuously absent.
Only small modifications from the first edition can
be noted in Chapters 5 and 8, which treat metal carbonyl and
alkyne (e.g., Pauson-Khand) chemistry, respectively.
Chapter 6 deals with metal carbene chemistry and is considerably
expanded in the sections on group 6 carbenes,
Rh(II)-catalyzed decomposition of diazo compounds, and ring closing
metathesis. Although the reference section on the last topic has
been updated, the space given to the discussion of RCM
strategies in the text does not yet reflect the major significance of this
new organometallic process or the wide range of new catalysts
that have been discovered recently.
In Chapter 7, a new section on metal-catalyzed
cycloadditions has been added. The p-allyl chemistry of
palladium now includes a discussion of asymmetric induction,
and new chemistry of metal arene complexes has been added
to Chapter 10.
Unfortunately, with the introduction of new, more
complex examples in this edition, the number of
typographical errors and omissions in the schemes has ballooned. While
the lack of information on yields, selectivities, solvents,
temperature, or reaction times in the schemes will force some
readers to go to the primary literature to get the complete picture,
students might be more negatively affected by the relatively
large number of structural typos in the schemes. These range
from the cosmetic (page 66, Figure 4.3--a renegade wedge;
inappropriate substituents in eq 4.57) to lack of
stereochemical markers (eq 4.51 on page 81) to wrong products (eqs
4.59, 4.98, 4.100, 4.108) and ghost referrals (eq 4.37 on line
8, page 76), to name just a few. One can only hope that
the publisher is already working on a revision in which
these distracting errors have been weeded out.
In summary, the second edition of this unique text
by Hegedus is significantly updated over the first edition
and continues to provide a very valuable and reasonably
priced resource on the practical uses of transition metals in
synthetic organic chemistry.
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