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Book Review Challenges in Synthetic Organic Chemistry. By T. Mukaiyama

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BOOK REVIEWS
Acronyms and Abbreviations in Molecular Spectroscopy. An
Encyclopedic Dictionary. By D. A . W Wendisch. Springer,
Berlin 1990. 314 pp., hardcover DM 98.00.-ISBN
3-540-51 348-5
This book entitled “Acronyms and Abbreviations in
Molecular Spectroscopy : An Encyclopedic Dictionary” by
D. A . W Wendisch is a comprehensive collection of the
jargon used by spectroscopists, which is rich in abbreviations. Of the approximately 500 entries, an overwhelming
majority are concerned with abbreviations used in NMR
spectroscopy; other spectroscopy methods such as ESR,
NQR, IR, Raman, optical spectroscopy, and polarized light
methods receive only minor coverage. To that extent, therefore, the description “Molecular Spectroscopy” in the title
promises more than is contained in the book.
Each entry includes an explanation varying in length from
a few lines to several pages. At the end of each section there
are relevant literature references, mostly to recent publications. The choice of keywords is very comprehensive for the
field of NMR, but is rather limited for the other areas of
spectroscopy. Of the NMR keywords that occurred to this
reviewer, not a single one had been omitted. On the other
hand, though, many terms that are not normally abbreviated
have been forced to fit into the procrustean bed of abbreviations and acronyms, and have thereby been altered out of
recognition in some cases. Thus, POF stands for “product
operator formalism”, WST for “water suppression technique”, and CDRE for “convolution difference resolution
enhancement”. I have not previously encountered the abbreviation POF in any publication, but have certainly seen
“product operator formalism” for which there is no entry in
this encyclopedia. This shortcoming detracts a little from the
books value as a reference source.
The explanations vary greatly in their extent and depth.
For example, under CYCLOPS I would expect to find not
only that it provides a way of avoiding instrumental errors in
data acquisition, but also an additional line of text giving the
phase cycle. WALTZ is described as a pulse sequence for
heteronuclear decoupling, but again the pulse sequence is
not given. Some rather unimportant sequences such as UPT
are given the rare distinction of a detailed description with a
diagram of the pulse sequence, whereas important sequences
such as HMQC or DEPT are described by text alone; only
four lines are devoted to DEPT, the most important of all
editing sequences ! This very uneven treatment of different
entries does not appear to follow any kind of system, and it
Angew. Chem. hi.Ed. Engl. 30 (1991) No. 10
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is regrettable that there is no correlation with the relative
importance of the entries.
Apart from these imbalances in the descriptions, which
could give non-specialists a wrong impression of the relative
importance of the various techniques, the explanations are in
general accurate and provide a good starting point, not least
through the literature references given. However, it would be
unreasonable to expect a complete coverage of all the important publications relevant to a given entry.
A further positive feature is the references that are given to
software packages for the analysis or simulation of NMR
spectra, such as LAOCOON, DAISY, SPHINX, or
SMART; on the other hand, commercial programs such as
Felix or the nmri products are not mentioned.
An index of keywords at the end of the book allows one to
quickly assign each term to the relevant area of spectroscopy. Here the extreme bias of the encyclopedia towards NMR
becomes obvious, even if it has not been noticed earlier. The
book is printed on glossy paper with a hard cover. The printing error on the cover is not typical of the rest of the book.
The figures are of good quality.
Despite the weaknesses mentioned above, the book can be
recommended as a work of reference for NMR spectroscopists. It provides an alternative to the recently published
book “A Handbook of Nuclear Magnetic Resonance” by R .
Freeman; although the explanations in the latter are more
detailed and well-balanced, the number of terms included is
much smaller.
Christian Griesinger [NB 1122 IE]
Institut fur Organische Chemie
der Universitat Frankfurt am Main (FRG)
Challenges in Synthetic Organic Chemistry. By T Mukaiyama. Oxford University Press, Oxford 1990. 225 pp., hardcover E 27.50.-ISBN 0-19-855644-6
To mark his 60th birthday Teruaki Mukaiyama wrote a
comprehensive review of his research efforts during the last
forty years. He describes all his research achievements
chronologically. Thanks to J. E. Baldwin, who has written a
fitting foreword, we can now read this fine book in English.
The importance of Mukaiyama’s contributions becomes
immediately clear just by browsing through the book. The
development of the oxidation-reduction condensation was a
real breakthrough in the development of organic synthetic
methods. Many macrolide syntheses still rely on the use of
the combination of triphenylphosphine and dipyridyl disulfide for the ring closure. The Mitsunobu reaction, developed
by a former collaborator of Mukaiyuma, is one of the most
reliable transformations to obtain a carbon-heteroatom
bond with inversion. Finally 2-halopyridinium salts as
reagents for esterification and macrolactonization have been
widely used in organic synthesis. The titanium(rv) chloride
catalyzed crossed aldol reaction between silyl enol ethers and
acetals is one of the most important C-C bond-forming reactions in organic chemistry. Since the first pioneering reports
of Mukaiyama’s group an enormous number of applications of titanium(1v) chloride have been reported. The use of
Lewis acids for the aldol reaction made it possible to achieve
high and synthetically useful stereoselectivities. At least as
important are the contributions of Mukaiyama’s group to
the development of the tin and boron enolates. Finally, the
Verlagsgesellschaft mbH, W-6940 Weinheim, 1991
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use of proline-derived chiral auxiliaries for the stereoselective reduction of ketones and for the stereoselective addition
of organometallic reagents to carbonyl compounds is yet
another achievement of Mukaiyama’s group.
That the author succeeds in accurately and impartially
describing all these results and many more which have been
accomplished in his laboratories is an astonishing achievement. Personal views intrude only rarely, and the results are
reported in essentially chronological order. Only in the prologue and in the epilogue does Mukaiyama allow himself
some personal remarks. In the first, poetic sentence of his
prologue he proclaims the importance of purely exploratory
experimentation. He advocates the importance of the unpredictable as a tool to achieve major breakthroughs in chemical research. One of the most fascinating parts of his book is
the well-documented change of Mukaiyama’s interest from
mechanistic questions to the development of synthetic methods. A series of unexpected results led him to develop the
oxidation-reduction condensation. In spite of the clear distinction made between the different research projects described in the individual chapters, a Western reader is surprised to find how all the innumerable experimental results
seem to be connected by an invisible network of associations.
The fact that most of Mukaiyama’s inventions of new reactions can be traced to the concept of “dehydration” may be
astonishing for Western chemists, but perhaps reflects some
of the Japanese traditions.
Keeping this in mind, the book is not only a source book
for the synthetic chemist about the results of one of the most
successful research groups in Japan, but also affords some
insights into the Japanese way of doing research.
Reinhard Neier [NB 1163 IE]
Institut fur Organische Chemie
der Universitat Fribourg (Switzerland)
Atomic and Molecular Clusters. Edited by E. R. Bernstein.
Elsevier, Amsterdam 1990. 806 pp., hardcover DFI
495.00.--ISBN 0-444-88193-X
Although research on clusters is still a relatively young
field, its close connections with atomic and molecular
physics, solid state physics, and not least with chemistry,
have resulted in it already becoming an extensive field of
study in its own right. This book does not attempt to present
a superficial review of all the different areas of cluster
physics. Instead some of the most important aspects of cluster physics have been selected and described in detail in eight
independent chapters. Each chapter is carefully constructed
and thoughtfully worked out, presenting valuable information in a clearly comprehensible style.
The first chapter, by R. E. Smalley, gives a comprehensive
62-page review of studies on clusters of carbon atoms. Special attention is devoted to the cluster c,,, which according
to the author will possibly “come to be recognized as one of
the most abundant and most important molecules in the
universe”. If this raises some doubts in the reader’s mind, he
or she will presumably feel a need to read this fascinating
chapter.
The next chapter is a comprehensive and well-written account of clusters of main group elements. In preparing this
the authors, M . L. Mandich, u! D . Reents, Jr. and V. E.
Bondybey, have performed an important service for the clusters research community. This substantial 290-page review is
packed with useful information, and contains nearly 500
literature references. It is the only such report in the clusters
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Ver~Rgsgese#schRflmbH, W-6940 Weinheim, 1991
literature, and is enough in itself to make the book a worthwhile purchase.
Chapter 3 is devoted to a specialist topic, the structures of
weakly bound complexes. In this 34-page article S. E.
Novick, K . R. Leopold, and u! Klemperer have tabulated the
most important properties of 144 complexes.
In Chapter 4 R. 0. Watts reports on recent advances in the
IR spectroscopy of van der Waals clusters. Reducing the
temperature of such clusters by adiabatic expansion and
laser cooling makes it possible to obtain IR spectra of previously unattainable resolution.
The following chapter is also concerned with van der
Waals clusters, though in this case with a special class, namely clusters made up of inert gas atoms and halogen atoms.
K. C. Janda and C. R. Bieler describe how such clusters exhibit a wealth of interesting effects, including the so-called
“rotational rainbows” and quantum interference effects associated with vibrational predissociation.
In Chapter 6 A. W Castlemann, Jr. and R. G. Keese describe a number of important techniques for observing clusters in a cluster beam, together with the interpretation of the
results from such measurements. Special attention is given to
the technique of resonance enhanced multiphoton ionization
of clusters followed by detection in a time-of-flight mass
spectrometer.
Chapter 7 represents another substantial contribution by
this book. In this 200-page article the editor, E. R . Bernstein,
describes the properties of a special class of molecular clusters consisting of two or more different molecular species,
usually organic, one of which is spectroscopically active. By
applying absorption and emission spectroscopy to molecular
clusters of this type, together with computer simulations, one
can investigate the ground and excited states.
The eighth and final chapter is a well-written review by
R. L. Whetten and M . I:Hahn of the spectroscopy of large
molecular clusters. It includes discussions of the liquid drop
model, the elementary excitations, and the liquid-solid transition in molecular clusters.
This book succeeds in the aim of filling the gap between
international conference reports and general reviews. The
wealth of information that it contains should make it a welcome addition to the library of every cluster physicist.
Thomas Lunge and T Patrick Martin [NB 1114 IE]
Max-Planck-Institut fur Festkorperforschung,
Stuttgart (FRG)
Quasicrystals, Networks, and Molecules of Fivefold Symmetry. By I. Hargittai. VCH Verlagsgesellschaft, Weinheim/
VCH Publishers, New York 1990. xiii, 314 pp., hardcover,
DM 14%.00.--ISBN 3-527-27927-X/O-89573-723-X
The discovery by Shechtman et al. in 1984 of a material
that exhibited the diffraction properties of an ordinary crystal (Bragg peaks) and yet seemed to display perfect fivefold
rotational symmetry has brought on a surge of activity in
solid state chemistry and physics. The output of the scientific
community in this area has been very large indeed, and the
need for monographs, both as introductions to the field and
as overviews, is obvious. The present book is therefore timely
(although not unique, as a fair number of monographs on
the subject have already appeared).
The book covers an area ranging from pure mathematics
to organic chemistry, thus providing a good overview to
newcomers and experts alike. Like any monograph consisting of a number of papers by different authors, it suffers
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Angew. Chem. Int. Ed. Engl. 30 (1991) No. 10
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