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Book Review Syntheses of Fluoroorganic Compounds. By I. L. Knunyants and G. G. Yakobson

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An Introduction to Organometallic Chemistry
Despite the strong tradition of organometallic chemistry
that exists in the German-speaking world, there has for
several decades been a lack of secondary literature in that
language which combines the qualities of competent expertise, balanced content, a modern style, and convenient
presentation. Christoph Elschenbroich and Albrecht Salzer
are therefore to be applauded on having now written a
textbook based on their obviously excellent course of lectures on the subject, namely:
Organometallchemie. By Ch. Ekchenbroich and A. Salzer.
Teubner, Stuttgart 1986. 472 pp., paperback, DM
42.00.--ISBN 3-5 10-03501-4.
The response of this reviewer to the authors’ commendably self-critical reflections in their preface is that no-one
else has ever achieved so much as they have done here!
Furthermore, I predict that this will be a unanimous verdict on the book.
The authors, in a very clever and instructive presentation
based on examples, have managed to extract, from the cornucopia of organometallic reactions, compound classes
and structures, all the important concepts which have become firmly established in this interdisciplinary and complex branch of modern chemistry. The contents are arranged in a conventional way according to groups of elements (“Main-group organometallics, pp. 23-196), types of
ligands (“Transition metal complexes”, pp. 218-384), extent of aggregation (“Metal-metal compounds and transition metal atom cluster compounds”, pp. 385-410), and
applications (“Organometallic homogeneous catalysts”,
pp. 412-441). Nevertheless, the danger of merely producing a list of compounds and reactions has been recognized
and avoided, and the contents of the chapters are well balanced one with another. The authors’ boldness in simplifying the subject matter works to the reader’s advantage by
stimulating him to reflect further on principles of reactivity
and structure, and helps him to recognize the broad features which are common to the organic chemistry of maingroup and sub-group elements. Thus, from the unavoidably large mass of chemical data, there emerges again and
again the underlying plan of this student text, which is
based on showing the resemblances and differences in behaviour between the elements. At points where a deeper
understanding of relationships of a more far-reaching and
general nature becomes necessary, the authors include “digressions” into fundamental aspects of spectroscopy and
bonding theory. This type of presentation will be much appreciated, especially by advanced chemistry students such
as graduates working for higher degrees. However, these
are by no means the only groups of readers who will find
the book useful. An industrial chemist too could save himself much time by reading up on modern catalytic processes in Elschenbroich and Salzer; he would, moreover, obtain an economically priced source of instruction in this
subject, and a review of new developments which are at
present mainly of academic interest, such as multiple
bonds between atoms of silicon or transition metals, or
methods for synthesizing cluster compounds. At the price
of DM 42 this 470-page book is within everyone’s means.
University and technical institute lecturers too will not
only thumb twice through this book, once from front to
back, then in reverse, and not just for mere curiosityland
will then reward the authors with gratitude and admiration. We will all learn from the book, will discard o u r old
lectures and insert new material, will refer back to other
monographs cited therein-in short, we will work from
this book!
Compared with other books in the field of organometallic and organo-heteroelement chemistry, including those in
English, “Elschenbroich and Salzer” is a unique achievement, which one hopes will have a stimulating effect on
future standards in the secondary chemical literature. In
view of this high recommendation, it would seem churlish
to search for printing errors in this first edition.
Wolfgang A. Herrmann [NB 822 IE]
Anorganisch-chemisches Institut
der Technischen Universitat Munchen, Garching (FRG)
Syntheses of Fluoroorganic Compounds. By 1. L. Knunyants
and G. G. Yakobson. Springer, Berlin 1985. vii, 299 pp.,
bound, DM 218.00.-1SBN 3-540-15077-3
Despite having been shortened to one volume, this English language version of the two-volume Russian work with
the same title still contains more than 300 synthetic methods for organofluorine compounds. Apart from a few descriptions of preparative methods for intermediates, the
methods nearly all originate from the relevant laboratories
of the Soviet Academy of Sciences. They have previously
been published in Russian language scientific journals, but
English translations exist in only a few cases. This book
therefore provides specialist readers with details, not readily accessible elsewhere, of experimental work in Russian
centers of research in organofluorine chemistry. It is probably the first such publication on this specialist topic in the
English-speaking world.
Some of the method of presentation in this book is undoubtedly borrowed from the well-known “Organic Syntheses” series. A single self-contained chapter is devoted to
each compound, the same formal sequence of presentation
being maintained for each substance. After the chemical
name, the structural and molecular formulae, molecular
weight, and physical data (so far as these are known), a list
of the most important published methods of preparation is
given, followed by the experimental details of the method
itself. I n some cases the chapter concludes with a list of
other compounds having similar structures which can be
prepared by the same method. Evidence of revision of the
previous edition is seen in the inclusion of comments on
critical features of the preparative method described.
The book is divided into three sections, each having a
systematic structure. Each section begins with methods for
preparing fluorinated hydrocarbons, then deals with derivatives containing other halogens as substituents, and
then, so to speak following the conventional structure of
an organic chemistry textbook, treats compounds which
contain the various functional groups. Each section concludes with a list of the numerous literature references
cited in the text. Subject and formula indexes at the end of
the book facilitate searching for particular compounds.
The first section deals with “Fluoroaliphatic Compounds”, and has been compiled by a team of authors at
the Moscow laboratory of the Soviet Academy of Sciences.
The main emphasis is on the chemistry of fluoro-olefins
Anqew. Cliem. Int. Ed. Engl. 26 (1987)
No. 7
and their derivatives, in particular the highly toxic compound octafluoro-isobutene (LCs,,=0.5 ppm!).
The main subject of the second section, entitled
“Fluoroaromatic Compounds”, are the perfluoro-arenes,
on the basis of which the Novosibirsk research group led
by G. G. Yukobson has developed an extensive area of
chemistry, here described in a very expert fashion.
L. M . Yagupolski et al., of the Kiev laboratory of the
Soviet Academy of Sciences, have produced the third section on “Aromatic Compounds with Fluorinated Side
Chains”. The main type of fluorinated side chain dealt
with is the trifluoromethyl group. As one would expect, the
conversion of carboxyl groups into CF3 substituents using
SF, assumes an important role here, whereas only a few
examples of fluorine-chlorine exchange in the corresponding chlorinated starting materials using SbF3 are given, and
that using hydrogen fluoride is not mentioned at all.
This compilation of synthetic methods for organofluorine compounds is not only of interest to organofluorine
chemists in academic or industrial laboratories. It is also of
value to the preparative organic chemist, as the methods
have generally been chosen such that no special equipment
is needed to put them into practice; information is also
given in an introductory chapter concerning the toxicities
of the most important fluorinating agents and reactive
fluorine-containing products, together with advice on handling them.
The positive impression gained from the book as a
whole is somewhat diminished by an abnormally large
number of printing errors in the text and structural formulae, leaving the user with a feeling that, for whatever reason, careful correction of the proofs has been omitted.
Giinter Siegemund [NB 817 IEJ
Hoechst AG, Frankfurt am Main (FRG)
High-Performance Liquid Chromatography in Biochemistry.
Edited by A . Henschen, K.-P. Hupe, F. Lottspeich, and
W. Voelter. VCH Verlagsgesellschaft, Weinheim 1985.
xiii, 638 pp., bound, DM 198.00.--ISBN 3-527-26057-9
Practice of High-Performance Liquid Chromatography.
Edited by H . Engelhardr. Springer, Berlin 1986. xii, 461
pp., bound, DM 198.00.--ISBN 3-540-12589-2
Biochemical research is scarcely imaginable without the
use of chromatographic methods for analytical and preparative work, and the latest high performance versions have
vastly improved the precision and speed of separations
and the accuracy of quantitative analysis. The first of these
two books, which includes contributions from authors in
the German-speaking world, is of great interest to all who
work in this field, since, following the appearance of a
number of symposium volumes and one less successful attempt at the topic (Hancock and Sparrows: HPLC Analysis of Biological Compounds), we now have for the first
time a complete summary of the basic principles and scope
of applications to all the relevant classes of substances.
The book has as its introduction three chapters which
deal with the fundamentals of chromatography, the column as the heart of the chromatographic set-up, and the
remaining experimental requirements for analytical and
preparative work. The presentation of this material is relatively condensed, but is essentially adequate as a basis for
beginners. However, the instrumentation section really
does no more than list components, without discussing the
advantages and disadvantages of different arrangements.
A further group of articles deals with individual classes
of substances: amino acids, peptides and proteins, peptide
Anqen, Chem. Int
Ed. Engl 26 (1987) No. 7
hormones, biogenic amines, lipids, carbohydrates, nucleic
bases, nucleosides and nucleotides, porphyrins, steroidal
hormones, vitamins, organic acids, and substances present
in plant tissues. These articles contain many illustrations
and typical examples of separations, and details of columns and mobile phases that can be used, usually summarized in the form of tables with a more detailed discussion in the text. Information is also given on detection
problems and the optimized pre-treatment of the sample,
which in biological materials often includes an extraction
step. Unfortunately the details of the methods are not always collected together in a form which stands out clearly
from the text, in the way that they are set out in the example given for the section on porphyrins.
The subject index and bibliography are very comprehensive, though the literature cited extends only u p to 1981 in
some cases, and in no case later than 1982. Thus, as often
occurs in books of this kind, topicality has been sacrificed
in favor of keeping to a pristine appearance of the text, a
policy which one must sometimes feel to be a disadvantage
in such a fast changing field. This can be seen in the case
of proteins, where it has not been possible to take account
of the very extensive knowledge gained recently on retention mechanisms for biological macromolecules and on the
mechanisms and kinetics of denaturation in contact with
the carrier. The latter point is, in fact, of considerable importance, since it has now led to a shift of emphasis away
from reversed phases towards biocompatible systems (ion
exchange chromatography, hydrophobicity chromatography, and affinity chromatography).
However, despite the above shortcoming this is a book
which will deservedly become a standard work on the subject, and its purchase can be well recommended, even for
inclusion in one’s personal collection. Against the general
tendency to deal with ever narrower specialized topics, this
book brings together theoretical fundamentals and practical applications in a form which is suitable even for newcomers, and at the same time affords a look out beyond
one’s own “backyard fence”.
The title of the second book could easily lead to misunderstanding. This work, written through the collaboration
of an international team of authors, is definitely not intended as a general source of advice on HPLC laboratory
practice; instead it deals with a few selected aspects,
mainly of a practical nature, burdened with only a little
theory. Separation mechanisms are discussed in detail only
in two of the chapters, on liquid-liquid chromatography
and o n ion pair liquid chromatography. Other sections
which treat questions of general importance are those on
quantitative analysis, special requirements for high resolution preparative work, and sample preparation together
with methods for automating it. The chapter on column
switching techniques also includes discussions on pre-concentration from complex mixtures, and on the removal of
interfering substances before analysis. This group of topics
is introduced by a descriptive list of the various components available for HPLC systems, which is impressive in
its wide scope and completeness, including even automatic
control equipment and data recording (although columns
are not included!). The various ideas are not simply listed,
but are discussed.
The second half of the book is devoted to applications,
which include a wide variety of fields such as forensic
chemistry, the separation of lipids, analysis of natural and
synthetic drugs, analysis of psychotropic substances in
body fluids, HPLC of amino acids and proteins, the separation of nucleic acid metabolites present in physiological
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