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Book Review Friedel-Crafts and Related Reactions. Edited by G. A. Olah

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In the preface Barnann-Myrback’s book (published in 1941)
is recommended, but there is no reference to “Methods in
Enzymology”(vo1ume 1 appeared in 1955) or to “HoppeSeyler/Thierfelder” (whose publication began in 1953), and
this is characteristic of the whole book. It is unintelligible why
the editors agreed to translation of a six-year-old book
without thorough revision. A purchaser who cannot examine
the book before buying it and therefore relies on the repute
of the authors will not discover for some time that he could
have spent his money to better effect in other ways. In its outdated form this book cannot be recommended.
H. Sund
[NB 498 IE]
The Molecules of Nature: A Survey of the Biosynthesis and
Chemistry of Natural Products. By J. B. Hendrickson. The
Organic Chemistry Monograph Series. Editor R. Breslow.
W. A. Benjamin, Inc., New York 1965. 1st ed., xiii,
179 pp., bound 57.00.
Submicro Methods of Organic Analysis. By R . Belcher. Elsevier Publishing Company, Amsterdam 1966. 1st ed.,
ix, 173 pp., numerous illustrations, bound, Dutch fl. 27.50.
The multitude of compounds nowadays can be arranged in a
logical scheme on the basis of their biogenesis. Thus the first
chapter surveys the biogenesis of the acetogenins (compounds
synthesized from acetate, a better and more comprehensive
term being “polyketides”), terpenes, and alkaloids. The
emphasis is placed on the presentation of the chemical
reactions, while the biological aspects are scarcely mentioned.
The student could easily gain the impression that all the
reaction paths described have been experimentally verified,
though this is by no means the case.
In this book, Belcher presents a summary of the submicro
methods of organic analysis, which he and his school have
systematically studied since 1951. The methods require 30 to
50 microgram samples, corresponding to a hundredfold
decrease in sample size as compared with the classical micro
methods. At present, however, they can be applied only to
solids.
The organisation of the book corresponds to that of Pregl.
The balance and the principal tools are described first. This
is followed by the methods for the determination of the
elements and of the functional gmdps, and the discussion is
concluded with the detarmination of molecular weights. The
only important determinations omitted are those of oxygen,
the saponificatian value and the hydroxyl value. The
methods used in most cases are conventional titration
methods adapted to the submicro scale. According to the
author, IP the very detailed procedures are adhered to, the
“maximum errors” are no higher than in the micro methods.
The methods described in this book, however, are not intended to replace the classical methods, but are designed to be
used when not enough substance is available for examination
by milligram or decimilligram methods. In these cases this
book will be of great assistance.
W . pfab
[NB 515 IE]
Friedel-Crafts and Related Reactions. Edited by G. A . Olah.
Vol. 1V: Miscellaneous Reactions, Cumulative Indexes.
Interscience Publishers, a Division of John Wiley & Sons,
New York-London-Sydney 1965. 1st Edit., 1191 pp.,
numerous’tables, bound f 17/-i ~.
Volume IV completes a bold and successful literary project.
Since the word “related” includes all acid-catalysed reactions,
whether they proceed in the presence of Lewis acids or
Bronsted-Lowry acids, the subject matter touches on almost
every field of organic chemistry. The reviewer has repeatedly
had occasion to recommend the earlier volumes (11. The last
eight chapters are of the same quality in their conciseness and
selection of material. These are followed by an extensive
(870 pp.) and carefully edited author and subject index for
the entire work.
The last volume deals in turn with the reactions of ethers,
including cyclic ethers (F. Johnson), the reactions of aromatic
compounds with Lewis-acidic metal halides (P. Kovacic),
and the reactions of nnn-benzendld aromatic compounds by
K. Hafner and K. L. Moritz. These are followed by somewhat
brief accounts of reactions with organometallic compounds
(G. A . Russell), reaction5 in organophosphorus chemistry
(G. M. Kosclapof,,, and reactians in carbohydrate chemistry
( W. Wagner). The second to last chapter (C. A . Olah and H .
W . Qarinn) deals with metatbetic reactions of salts, and G . A .
Olah finally presents a review of applications.
It is to be hoped that the highly informative character of
“Friedel-Crafts and Related Reactions” will be maintained
in the future.
J. Cosselck
[NB 544IEl
~.
[ I ] Cf. Angew. Chem. 78, 499 (1966); Angew. Chem. internat.
Edit. 5 , 531 (1966).
Angew. Chem. internor. Edit.
Vol. 5 (1966) j No. I 2
This book is one of a series of monographs intended to
supplement the elementary instruction of undergraduate
students in organic chemistry. The author rightly points out
that the student today often is not acquainted with the
fascinating problems of natural-product chemistry. The
purpose of this book, therefore, is to fill this gap, and the
author has succeeded admirably in achieving this aim.
In the following chapters, the chemistry of these classes of
natural produots is described with the aid of a few wellchosen examples. The reader is brought into contact with
both the classical degradation reactions and the modern
methods of structure elucidation. Stereochemical questions
are discussed at various points.
Exercises, the solution of which will cause some trouble even
to advanced workers, are skilfully fitted into the text, and
the entire book demands intense participation on the student’s part. The printing and the reproduction of formulae
are excellent. The book is strongly recommended to the
advanced chemistry student.
H. Grisebach “€3 518 IE]
Interpretation of Organic Spectra. Edited by D. W. Marhieson.
Acadcmic Press Inc., London-New York-Sydney 1965.
1st ed., IX, 179 pp., numerous illustrations, cloth $7.00.
The increasing use of spectroscopic methods for the determination of thz structures of organic compounds presents a
need for the teaching of these methods. The present book is
based on practical exercises in summer courses; with the aid
of examples (17 in N M R , 15 in infrared, and 10 in mass spectroscopy), it provides a practical introduction to the three
most important methods of structural elucidation. The analysis of number of examples is first demonstrated in fair detail
without previous description of the fundamental principles, in
order that the reader may then be presented with spectra, without further explanation (but with solutions), to work out for
himself.
Didactically and in the selection of the material the individual
sections, unfortunately, are of varying standard. The N M R
and infrared sections probably offer the newcomer a better
introduction than the section on mass spectroscopy, which
(e.g. in Problem 5 ) gives unnecessarily difficult examples, and
does ngt refef.to literature l a t d than about 1958. The discussion of N M R data is concise and t o the point, that of
infrared a n d mass-spectroscopic data is rather lengthy; the
infrared section evinces a pessimistic, critical attitude, while
the other two sections offer the reader more hope of success
in the analysis of spectra. In contrast t o the pleasing external
presentation of the book, one gains the impression on
reading that some points in the text, in the formulae, and
in the terminology have not been as carefully worked out as
is necessary, particularly in a book intended for teaching.
In the critic’s opinion, this book is not to be recommended, at
least for the beginner.
W. Liittke
[NB 505 IE]
1053
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