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Book Review Synthesis of Sulphones Sulphoxides and Cyclic Sulphides. Edited by S. Patai and Z

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BOOKS
it is intended for anyone taking Prozac,
considering taking it, or wanting to stop
taking it, as well as for the families and
physicians of anyone suffering from depression. It deserves to be as well known as
or even better known than Kramer’s book,
which has received an incredible amount
of publicity. Because the two books are
complementary, they should be read together. Caveat aeger! (Let the patient beware!)
George B. Kauffman
Department of Chemistry
California State University
Fresno, CA (USA)
Synthesis of Sulphones, Sulphoxides
and Cyclic Sulphides. Edited by S .
Patai and Z . Rappoport. Wiley,
Chichester, 1994. 720 pp., hardcover
& 175.00.-ISBN 0-471-93970-6
The book reviewed here belongs to the
series The Chemistry of Functional
Groups, which began over 30 years ago
and is of great importance to synthetic
chemists. As noted by the editors in the
preface, this volume is the last in the current series of updated versions. It contains
seven chapters by well-recognized authors, dealing mainly with synthetic aspects of open-chain and cyclic sulfones
and sulfoxides, as well as cyclic sulfides.
Three of the chapters (Ch. 1 : “Synthesis
of Open-Chain Sulfones”, by K. Schank;
Ch. 3: “Synthesis of Sulphoxides”, by J.
Drabowicz, P. Kielbasinski and M. Mikolajczyk); Ch. 5: “Cyclic Sulfones and Sulfoxides”, by U . Zoller) are identical with
Chapters 7-9 of the volume The Chemistry qf Sulphones and Sulphoxides, published in the same series in 1988 (review: J.
Voss, Angew. Chem. Int. Ed. Engl. 1989,
28, 1070). The latest developments in
these areas (since 1986) are covered in the
form of appendices (Chapters 2,4, and 6).
These follow the same structure as Chapters 1, 3, and 5, and the numbering system
for the reaction equations, tables, and literature references continues directly on
from the preceding chapters, so that one
can easily compare the two and quickly
find out about the latest research. The literature up to 1992 is covered thoroughly,
extending in some cases up to early 1993.
The lengths of these “appendix” chapters
are clear evidence of the rapid developments in the last few years on many aspects of the chemistry of sulfones and
sulfoxides. This is seen especially in Chapter 4, which is largely concerned with the
use of chiral sulfoxides for asymmetric
syntheses. All the authors have aimed at a
Angrw.
Uioni.
In!. Ed. B i g / . 1995, 34, No. 11
C
concise but well-balanced treatment. Unavoidably, the monograph Sulphones in
Organic Synthesis, by N. S . Simpkins,
published in 1993 by Pergamon Press, appeared too late to be cited in the bibliography.
The last chapter, “Cyclic Sulfides”, by
G . Capozzi, S. Menichetti, and C. Nativi,
seems to me to be of special importance
and a very welcome part of this book for
several reasons. Firstly, cyclic sulfides are
in many cases indispensable precursors
for the synthesis of cyclic sulfoxides and
sulfones, reactions for which a wide variety of effective oxidizing agents for different situations are now available. Secondly, the most important characteristic
properties of sulfur heterocycles with
three- to eight-membered rings, mainly
saturated, are here summarized in a single
chapter. The authors have concentrated
mainly on developments since 1980, while
not neglecting earlier results of fundamental importance. In addition the comprehensive bibliography to this chapter (698
references) allows rapid access to earlier
publications.
A minor point, but one that is unusual
in a monograph, is that the authors have
each been allowed to use their preferred
spellings “sulphur” or “sulfur” in the
names of the compounds discussed.
The volume contains a total of 3037 literature references and has carefully prepared author and subject indexes, which
contribute to giving it the true quality of a
handbook. It will be an extremely useful
source of information, not exclusively for
“sulfur chemists”, and should therefore
be available in every chemistry library.
Eberhard Wenschuh
Berlin (FRG)
Carbon-13 NMR Chemical Shifts in
Structural and Stereochemical Analysis. (Series : Methods i n Stereochemical Analysis. Series editor: A. P.
Marchand.) By K. Pihlaja and E.
Kleinpeter. V C H Publishers, New
York, 1994. 379 pp., hardcover
DM 150.00.--ISBN 0-89573-332-3
In the early 1970s, when I 3 C N M R
spectroscopy was approaching its full maturity, the effects of substituents on chemical shifts (substituent chemical shiftsSCSs) were important as an empirical aid
in the interpretation of spectra, and thus
in determining the structures of organic
molecules. Since that time the importance
of empirical correlations has declined as
new one-dimensional and multi-dimensional experimental techniques have beVCH Verla,qsgeseilschafrmbH, 0.69451 Weinhrim, 1995
come available. These yield “hard”
information (e.g., on scalar spin-spin
couplings or on the nuclear Overhauser
effect), making the “softer” information
based on chemical shift considerations
largely superfluous. This is a welcome development, as it puts structure determination onto a firmer basis and reduces the
necessity for interpretations that rely on
probabilities. Therefore, one might well
ask whether it is still appropriate to bring
out a book such as this one by the
Finnish-German team of Pihlaja and
Kleinpeter, which aims to stimulate an interest in I3CN M R chemical shifts and to
convince the reader of the usefulness of
such data in structural analysis. The answer to the question is a definite yes, because the book is mainly concerned with
the stereochemical aspects of 3C chemical shifts, and the most recent major
reviews on this subject appeared a considerable time ago, for example the articles in
Topics in Stereochemistry by Wilson and
Stothers in 1974 and by Duddeck in 1986.
The introductory chapter deals with
practical considerations. including a discussion of the assignment of I 3 C N M R
spectra. The advice given to the reader
seems somewhat arbitrarily chosen; the
tips are occasionally trivial (e.g., “peak
picking is strongly recommended”), and
owing to the shortness of the chapter its
value is rather limited. There is an error
on page 2, where it is stated that the improvement in signal-to-noise ratio using
quadrature detection compared with single-phase detection is a factor of
(where y2 is the number of accumulations);
the correct factor is
In the section on
“Referencing the Spectrum” it is of little
help to give only the chemical shifts of
undeuteriated solvents, and the information that deuterium isotope effects can be
as large as 1 ppm does not improve matters. In the spectra shown in Figures 1.5
and 1.6 the numbering of the peaks does
not entirely correspond to that in the
structural formula. The list of literature
references for Chapter 1 contains many
errors, especially in the names of authors,
which will immediately catch the reader’s
eye without even having to look up the
references: “Breitmeier’‘ for Breitmaier,
‘‘Hull’’ for Hill, “Schoolery” for Shoolery, “Bedall” for Bendall, “Submarian”
for Subramanian, and so on. The references attached to the later chapters also
show a lack of care.
The short second chapter deals in a general way with additivity relationships for
SCSs (and deviations therefrom), and
with the use of SCSs in structure determination and stereochemical assignments.
Chapter 3 then discusses in greater detail
fi
1/z.
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