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Book Review Organic Fluorine Chemistry. By M. Hudlicky

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Preparative Acetylenic Chemistry by L. Brandma. Else~im
Publishing Co., Amsterdam-London-New
York 1971.
1st Edit., x, 207 pp., 14 figs, 3 tables, bound E 8.20.
In a foreword written by his famous teacher, Prof. Arens,
the author is praised for the care with which the book is
written and for the usefulness of this collection of recipes,
which are arranged in nine chapters as follows: 1. General
practical information : 2. Preparation of metal acetylides;
3. Alkylations at the acetylene carbon and related reactions;
4. a-Hydroxyalkylation, -carboxylation, and -acylation at
the acetylene carbon; 5. Direct introduction of heterosubstituents ; 6. Preparation of acetylene compounds by
means of elimination reactions ;7. Base-induced migration
of the triple bond; 8. Various syntheses; 9. Starting compounds. Further information regarding the contents will
be found in a type index and in an index of empirical and
structural formulas, extending over some eight pages.
According to the author, this collection of recipes is not
intended merely for the specialist in the field; however, one
must mention in this context a very serious drawback,
namely that, incredibly enough, the book contains practically no literature references! By way of justification it is
explained in the introduction that the principles of Raphael,
Rutledge, Viehe, and Ziegenbein have been adequately dealt
with. There are thus practically no simple comparisons with
the original literature. However, if the critical user takes
the trouble to look up original works, he will often find
himself wondering why changes have been made without
comment or reference. Without this deplorable shortcoming this otherwise useful book would have been even
more recommendable.
Heinz Giinter Viehe [NB 108 IE]
Synthetic Methods of Organic chemistry. Vol. 25. By
W Theilheimer. S . Karger Verlag, Basel 1971. 1st Edit.,
xvi, 707 pp., bound DM 296.“Theilheimer”, which has been appearing annually for 25
years and which has now notched up 22357 selected abstracts covering all areas of preparative organic chemistry,
constitutes an invaluable aid to anyone carrying out
syntheses. The present volume contains abstracts of 700
original papers published during the period 1%8-1970.
This volume contains in addition the citations from volumes
21-24 in the text and in a comprehensive general index
(161 pages), which covers methods, compound classes, and
reagents. This makes the book much easier to use, especially
for those readers for whom the Weygand system on which
the arrangement is based represents a serious “energy
barrier” !
As in the past, the seven-page section on “Trends in Synthetic Organic Chemistry”, which contains a brief descrip
tion of synthesis methods and information of general
interest from the latest literature, is especially readable.
The use of India paper has made it possible to keep the
size ofthe current volume, which contains more information
than ever before, within reasonable limits. Apart from two
missing pages (550and 551) in the reviewer’s copy and some
absence of care in the drawing of a few steric formulas, the
printing and presentation are up to the usual excellent
In view of the plethora of abstract literature available to
the organic chemist at the present time, one might- be
tempted to question whether “Theilheimer’s” continued
existence is still justified. In the reviewer’s opinion no other
work can compare in the speed, detail, or clarity with which
“Theilheimer”abstracts the literature on synthetic methods.
It is therefore most desirable that students of chemistry
should become acquainted with the Weygand system at
the earliest possible stage.
Lutz-F. Tietze [NB 109 IE]
cbemishy. By M . Hudlicky. Plenum
Press, New York-London 1971.1st Edit. xiii 148 pp.,
numerous figures and 50 tables, bound $18 48.
Organic Fluorine
This book appears to be based on the manual published
by the same author in the late 1950’s, which was translated
into German in 1960 under the title: “Chemie der organischen Fluorverbindungen”. The great value of this fundamental monograph on organic fluorine chemistry lay in
the concise summary of methods, preparation routes, and
In comparison with the standard work, which has become a
“classic”, the present book contains no fundamental
changes. The first few chapters deal with fluorinating
agents and their use. The chapter “Analysis of Organic
Fluorine Compounds” has been placed earlier in the book,
and now contains brief notes on IR, mass, and fluorine
NMR spectroscopy.
The longest chapter deals with the reactions of organic
fluorine compounds. An introductory section on reaction
mechanisms presents a discussion of the inductive,
mesomeric, steric, and hyperconjugation effects for the
interpretation of the reactivity of fluorinated organic
compounds, which is rather superficial. The section
“Hyperconjugation”, for example, makes no mention of
the fact that this model has no physical significance. Valid
theories that should also have been used for the explanation
of mesomeric effects” are not considered.
In the reviewer’s opinion, any survey of this special field,
however detailed, is of little value at present without a
fairly profound discussion of the broader relationships.
The book can therefore be recommended at best as a
collection of facts.
H. J . Scholl [NB 116 IE]
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Pappdallee 3,
Angew. Chon. infernat. Edit. J Vol. 12 (1973) /
No. 2
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