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Book Review Organic Syntheses Based on Name Reactions and Unnamed Reaction. By A. Hassner and C. Stumer

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BOOKS
What's in a Name
Instrumental Methods for Determining Elements. By L. R. Taylor, R. B.
Pupp and B. D. Pollurd. VCH
Verlagsgesellschaft, Weinheim/VCH
Publishers, New York, 1994. 322 pp.,
hardcover DM 128.00, $ 5 1 S O . ISBN 3-527-28096-0/1-56081-038-6
This book is intended for the analytical
chemist who has to choose the most suitable method for a given problem. It treats
in detail all the most important modern
instrumental methods of elemental analysis: atomic absorption spectroscopy
(AAS), atomic emission spectroscopy
(AES), voltammetry, potentiometry,
chromatography, X-ray fluorescence, and
combustion methods. For each method
there is a brief description of the basic
physical principle and the construction of
the instrument. This information is intended only as a short introduction, and
not as a substitute for a thorough study of
the fundamentals of the method concerned. References to detailed specialist
literature in the form of monographs or
original papers are provided.
The authors then compare the various
methods with regard to their practical application, placing special emphasis on the
needs of the user who must decide on a
particular analytical method for the problem in hand. They consider questions
about the sample itself, including the nature of the matrix, sample size, and
sample preparation, economic factors
such as the capital and running costs of
the instrument, its complexity, sample
throughput rate, and possibilities for automation. A clear distinction is made between, on the one hand, purely instrumental factors such as limits of detection,
sensitivity, operating range, precision,
and selectivity, and on the other hand element-related matters such as capabilities
for multielement detection, for quantitative analysis, and for distinguishing between different species of the same element. The authors also discuss questions
such as how widespread is the use of the
instruments concerned (as this affects the
availability of information about applications), and whether the method can be
used for on-line process analysis. Each
chapter is rounded off by giving examples
(in the form of tables) of typical applications of the method, and information
about the main instrument manufacturers, which is useful for requesting promotional and technical information. As well
as the methods mentioned above, the authors also briefly discuss capillary electrophoresis, flow injection analysis, massspectrometric techniques, neutron activation analysis, and spectrophotometry.
The detailed discussions of the various
methods are helpful to the reader both in
choosing suitable analytical methods for
specific problems and, if the question arises, in purchasing a new analytical instrument. In this respect the book differs from
conventional texts in this field, which are
usually confined to treating in detail the
theoretical background and the areas of
application of each analytical method. Znstrumental Methods ,for Determining Elements is therefore a valuable additional
resource for the practical analyst.
Nicolas Braun
Hannover (FRG)
Namen- und Schlagwortreaktionen der
Organischen Chemie. By 7: Luue and
A . Plugens. Teubner, Stuttgart, 1994.
338 pp., paperback DM 36.80.ISBN 3-519-03526-X
r
This section contains book reviews and a list of
new books received by theeditor. Book reviews are
written by invitation from the editor. Suggestions
for books to be reviewed and for book reviewers
are welcome. Publishers should send brochures or
(better) books to Dr. Ralf Baumdnn, Redaktion
Angewdndte Chemie, Postfach 101161, D-69451
Weinheim. Federal Republic of Germany. The editor reserves the right of selecting which books will
be reviewed. Uninvited books not chosen for
review will not be returned.
A n g w . Chem In[. Ed. Engl. 1995, 34, N o . 8
Organic Syntheses Based on Name
Reactions and Unnamed Reactions.
By A . Hassner and C . Stumer. Pergamon, Oxford, 1994. 452pp., paperback s 28.00.-ISBN 0-08-040279-8
The Noyori homogeneous catalytic reaction for asymmetric hydrogenation will
certainly mean something to you. But are
0 VCH
VerlugsgesellsrhuffmhH. D-69451 Weinheim,1995
you also familiar with the Perkow synthesis
of vinyl phosphates? What d o you know
about the Neber rearrangement? Would
you like to be able to quickly find out
something about the Stork enamine reaction? The two books reviewed here can
help with such questions, rapidly and at
little cost. For the average reader it is still
just as important as ever to have rapid
access to information without using CDR O M or on-line services. Although summaries of important reactions already exist-for example, in the relevant section of
the Merck Index-these two books by
Hassner and Stumer and by Laue and
Plagens bring together information on important reactions of organic chemistry in a
very handy form that is convenient to use.
Although they are very similar in layout,
some clear differences emerge. The book
by Laue and Plagens, in the Teubner series
of student textbooks, has a striking external appearance with a somewhat more
careful standard of production, the typeface and the formulas being well matched
in size and pleasingly arranged. On the other hand the book by Hassner and Stumer,
in the Tetrahedron Organic Chemistry Series, is a compilation of pages produced
directly from the computer, and one is
struck by the large areas of empty space.
The Laue and Plagens book is intended
for students of chemistry, pharmacy, and
related disciplines, and contains clear descriptions, in alphabetical order, of some
130 important reactions of organic chemistry. These include both important name
reactions and others ("Schlagwortreaktionen", key-word reactions) that are
known by descriptive names rather than
being linked to the name of a scientist, e.g.
the di-n-methane rearrangement. As well
as classical examples such as the Finkelstein and haloform reactions, which are to
be found in any traditional textbook of organic chemistry, the compilation also includes many of more recent origin, such as
the Pauson-Khand reaction, the Bergman
cyclization, and the Dotz reaction. In each
case the title is followed by a one-sentence
description of the reaction and a generalized formula scheme. Next there is a brief
discussion in which the main emphasis is
on the reaction mechanism. Other relevant
information is also given; for example, in
0570-0N33195:OR08-0935$ 10.00+ .2S/O
935
BOOKS
describing the Cope rearrangement it is
pointed out that it should not be confused
with the Cope elimination reaction. The
cross-references to other reactions described in this book are very helpful. The
book also contains a short list of selected
literature references. giving not only the
first publication in which each reaction is
described, but also important review articles enabling the reader to find out about
a reaction of interest in greater depth. It is
pleasing that the authors appear to have
made an effort to include some quite recent citations extending into the 1990s.
Brief name and subject indexes are provided at the end of the book.
The book by Hassner and Stumer covers
about 450 reactions, including some lesser
known ones, again arranged alphabetically. In the preface the authors rightly point
out that for reasons of space alone it is not
possible to include every reaction. and
that some whose mechanisms are likely to
be well known to every chemist have been
purposely omitted. Nevertheless, in view
of the fact that many reactions of a highly
specialized nature have been included, it is
surprising to find no mention of the mechanistically important and highly topical
Bergman cyclization. In many cases several closely similar reactions have been included. Each reaction is first described in
a single sentence, which is then followed
by a formula scheme for a specific example of the reaction, giving the reaction
conditions and in many cases also the
yield. A few relevant literature references
are listed, including the first paper describing the reaction and at least one review article. Lastly the experimental details
for carrying out the example reaction are
given. At the end of the book are indexes
according to names, reagents, and reaction types, as well as a fold-out “Functional Group Transformations Index” similar to those provided in the Compendium
of Organic Synthetic Methods.
What are the main differences, and
which book should be recommended? The
book by Laue and Plagens is certainly
aimed more at the needs of students, and
from that standpoint the inclusion of brief
summaries of the mechanistic background
is an important advantage. By cleverly limiting the coverage to about 130 reactions
the authors have allowed themselves sufficient space to do justice to the didactic
quality expected from a book intended for
students. The book by Hassner and Stumer
is clearly intended rather for the research
chemist in academia or industry. For this
readership, although it may still be important to give mechanistic information, the
main need seems to be for rapid access to
typical experimental conditions for the re936
action of interest. Whereas Laue and Plagens can best serve to complete the reader’s knowledge, Hassner and Stumer on
the other hand is more in the nature of a
resource for solving preparative problems. For the latter purpose one is not
necessarily looking for a named reaction,
but it is a fact that many of the most important reactions carry the names of their
originators. What is meant in the title by
“Unnamed Reactions”? There are none
of these in the book-by definition they
cannot even appear in the “Names Index”. The authors have given every reaction (at least) one name in its heading.
Probably the purpose of this part of the
book’s title is just to attract the attention
of potential readers.
Both books are well suited to their different purposes and can be recommended-this reviewer is glad to have them
both. However, a word of caution is in
order. These books and others like them
are eminently suitable for quickly learning
about a large number of reactions of organic chemistry, and many readers will
certainly find them very useful, for example when preparing for examinations.
Nevertheless, both the readers and their
teachers must always bear in mind that
knowing about a reaction is no substitute
for understanding it. These books are not
intended as alternatives to more detailed
textbooks, but are for quick reference, and
are best treated as an extension of the textbooks to be used judiciously. No well-constructed examination can be limited to
merely asking about named reactions, and
equally the memorizing of a “data bank”
of reactions is not sufficient to enable one
to succeed as a scientist.
Holger Butenschon
Institut fur Organische Chemie
der Universitat Hannover (FRG)
Chemical Generation and Reception
of Radio- and Microwaves. B y A. L.
Buchachenko and E. L. Frankevitch.
VCH Verlagsgesellschaft, Weinheim, 1994. 180 pp., hardcover
DM 135.00.-ISBN 3-527-89630-9.
“Spin chemistry”, i.e. the investigation
and utilization of magnetic field effects
and spin effects in chemical reactions, enjoys increasing popularity. The authors of
the present book like to distinguish between two generations of spin chemistry.
The first was concerned with the influence
of static magnetic fields, typical examples
being magnetic field effects (MFE) or
chemically induced dynamic nuclear and
electron spin polarizations (CIDNP and
:(? VCH ~rlug.F~eselIs~hhuff
mbH, 0-69451 Wi,inhrim. I995
CIDEP). In this book the emphasis is on
spin chemistry of the second generation,
which comprises the interactions with additional oscillating fields. These cause
radio-induced magnetic isotope effects
(RIMIE), stimulated nuclear polarization
(SNP), and microwave-stimulated quantum beats, and are exploited in reaction yield detected magnetic resonance
(RYDMR). In addition, the authors deal
with the reversal of such processes, namely the emission of coherent microwave radiation from chemically reacting systems.
In the first chapter, “Magnetic Scenario
of Chemical Reaction”, numerous examples are given to drive home the principle of spin conservation during chemical
transformations and thus spin selectivity
of chemical reactions. The second chapter
is a discussion of the radical pair mechanism, despite its misleading title, “Magnetic Interactions in Chemical Reactions”. The title of the third chapter,
“Magnetic Effects in Chemical Reactions”, also slightly misrepresents its actual content: except for a few introductory
sentences, it only deals with spin chemistry of the first generation. “Chemically
Induced Radio-Frequency Emission” is
only touched upon in the short (1.5 pp.)
fourth chapter, although from the title
of the book one would have expected
this to be a central topic. Four chapters
on RYDMR (“Reaction Yield Detected Magnetic Resonance-RYDMR”,
“RYDMR in Solids”, “RYDMR in Liquid Solutions”, and “RYDMR in Photosynthetic Systems”) are followed by two
others (“Radio-Induced Magnetic Isotope Effect” and “Microwave-Stimulated
Nuclear Polarization”) about spin chemistry of the second generation. The authors focus on examples and applications
rather than on detailed quantitative explanations of the theory of these effects.
In Chapter 11 (“Coherence in Spin Dynamics and Chemical Reactivity”) quantum beats are discussed. At the end of the
volume we find a very short chapter
(3 pp.) on “The Action of Electromagnetic Waves on Biological Processes”.
The most striking impression one receives when going through the book for
the first time is that it is written in alarmingly bad English. A few examples, quoted verbatim, may illustrate this; there are
numerous others of this kind. There are
frequent misspellings of proper names“Plank constant” (p. 3), “Schrodinger
equation” (p. 18), “Gann-diode” instead
of Gunn-diode (p. 76), “Abraham” instead of Abragam (consistently on p. 12.5
and p. 127), and chemical names“vinilene” (p. loo), “acetonitryl” (p. 129,
“dinucleatide” (p. 130).
OS70-0S33!95jOXt~S-0936$ 10.00 i
,2510
Angrw. Chem. l n l . Ed. EngI. 1995, 34. N o . 8
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