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Book Review Methoden der organischen Chemie (Methods of Organic Chemistry) (Houben-Weyl) Vol.

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BOOK REVIEWS
Chemotaxonomy der Pflanzen. Eine Ubersicht iiber die Verbreitung und die systematische Bedeutung der Pflanzenstoffe. (Chemotaxonomy of Plants. A survey of the distribution and the systematic significance of plant substances).
Volume 4, Dicotyledons: Daphniphyllaceae to Lythraceae.
Chemical Series. Textbooks and Monographs in the Field
of the Exact Sciences. Birkhauser Verlag,_suttgarkBasel
1966. 1st Edit., 551 pp., D M 106.-.
Of the six projected volumes of this already very well introduced work, Volume 4 is now available. It deals with the
essential substances contained in a total of 71 dicotyledonous
plant families, namely (in alphabetical order) Daphniphyllaceae to Lythraceae. Approximately 28000 species are
included. The families Euphorbiaceae, Gesneriaceae, Labiatae, and Lauraceae are particularly large; the important
family Leguminosae is left for a later volume.
The plan and the presentation of the subject matter follows
the customary scheme. With supplements, the literature is
covered to about the end of 1965 and includes many difficultly accessible references. Misprints and factual errors are
rare, and the printing and presentation are as usual excellent.
The scientist interested in the results of phytochemical
research will find the volume very rewarding. Hegnuuer’s conclusions in regard to the systematic inclusion of debatable
genera are careful and conservative. Conclusions concerning
the families that are discussed often include sentences such
as: “For the time being the available data permit only a
superficial chemotaxonomic assessment. . .”. The situation
is likely to alter as soon as sufficient detailed chemotaxonomic
investigations become available. c,H. Eugster [NB 650 IEI
Die wissenschaftlichen Grundlagen des Pfianzenschutzes. By
H. Martin. Based o n the 5th Edit. (1964) o f The Scientific
Principles of Crop Protection, translated and supplemented
by K . J . Schmidt. Verlag Chemie GmbH., Weinheim/
Bergstr. 1967. 1st Edit., xi;, 696 pp. and 3 tables, D M 68.-.
The present book is divided into 16 chapters, the first of
which introduces the subject matter. Chapters 11, 111, and IV
deal with the resistance of plants to pathogenic agents and
pests, the influence of external factors on the susceptibility
of plants, and the methods of biologica1 pest control. Chapters V to XVI discuss the chemical and physical agents and
methods for the protection of plants, the problems that arise
in their use, mechanisms of action, and special questions
concerning the treatment of infection centers and vectors.
The translation has been supplement by valuable references
to recent publications, e.g. to recent German works on
biological pest control, to the “ultralow voIume” technique,
which involves the spraying of highly concentrated substances, to new methods for the production of insecticidal aerosols, t o the antibiotics Blasticidin-S and Kasugamycin, to
the phosphorus insecticides, which are not discussed in the
English text, to the mercury-free seed dressing Voronit, and
the use of simulated bat cries to scare insects. Tables giving
the Latin, German, and English names of important arthropods and fungi, as well as data on their classification,
are included as an appendix. The book ends with comprehensive subject and author indexes.
The translation contains a number of shortcomings and
printing errors, which should be corrected in a new edition.
Thus the fungicide “Nirit” is referred to as “Nitrit”, Dinocap
sometimes appears as “Dinocab”, Prometryn as “Prometrin”
and Ametryn as “Ametrin”. The statement that the herbicide
Linuron was “placed o n the market in 1960 by DuPont
Nemour Inc.” should also be corrected, since Linuron is a
product of Farbwerke Hoechst AG. (Seherer et nl., German
Patents, 1956 and 1958). The alkali metal and ammonium
salts of “3,5-dinitro-o-cresol” are not “soluble in all pro-
154
portions in water”; the solubility of the sodium salt at room
temperature is only 5 %. D D T is not readily soluble “in most
organic solvents”. Gamma-HCH contains no “cyclodiene
grouping”.
The common names recommended by the International and
the British Standards Organisations ( I S 0 and BSI) are
occasionally confused with trade names of crop protection
agents, e.g. in the cases of Carbaryl (“the B.S. trade name is
Carbaryl”), DNOC, and Dioxathion. In many cases the
common names used in English, e.g. Azinphos, Fenthion,
and Trichlorfon, are replaced in the translation by trade
names, while in other cases substances, such as Monuron,
Diuron, Neburon, and Linuron, are referred to by the
common names but not by trade names. This disorderly use
of names makes the book unnccessarily difficult to use. The
chemical names should all be formed in accordance with the
IUPAC nomenclature rules in the next edition.
The German translation of the article will be warmly received,
since the English author has succeeded brilliantly in providing
the biologically and agriculturally oriented reader with a clear
picture of the physico-chemical and toxicological aspects of
crop protection, and at the same time offering chemists and
toxicologists working on the synthesis and testing of crop
protection agents an insight into the biological problems
~
i [NB~686 IEI
~
encountered in crop protection. H. ~
Methoden der organischen Chemie (Methods of Organic
Chemistry) (Houhen-Weyl), Vol. VI, Part 3, Oxygen Compounds I, Edited by Eugen Muller. Georg Thieme Verlag
Stuttgart 1965.4th Edit., xlvii, 832 pp., 4 figures, 70 tables,
D M 212.-.
The present Volume VI, Part 3, Oxygen Compounds I, of
Houben-Weyl continues the sequence of monographs on the
methods of preparative organic chemistry in the accustomed
thorough manner.
The book begins with chapters on the preparation and transformation of ethers, acetals, orthocarbonates and oxonium
salts; the literature references for the ethers embrace those
up to and including 1962, and those for the remaining three
classes of substances to 1963.
These chapters, written by H. Meerwein, leave nothing to be
desired in respect of clarity of expression, completeness of
the synthetic procedures, and the amount of personal
experimental experience incorporated.
The following chapters deal with methods of preparing and
transforming epoxides, oxetanes, and dihydro- and tetrahydrofuran derivatives, with literature references up to 1963.
These chapters too are characterized by a strict systematic
arrangement and admirable thoroughness of treatment.
The chapter “Ethers” is subdivided into purely aliphatic,
aryl aliphatic, purely aromatic, and unsaturated ethers, so
that the variations of comparable procedures can be viewed
against the reactivities of the individual classes of substances.
It should be emphasized that the methods of sugar alkylation
are dealt with in a comprehensive manner; the biochemist
engaged in preparative work should derive particular benefit
from thb aspect. The methods of ether transformation embrace all the oxidation, cleavage, and rearrangement reactions
observed in ethers in systematic order. Consideration has been
given to the generally neglected steric factors in the addition
of alcohols to unsaturated ethers (p. 42).
The chapter on the methods of preparing acetals and ketals
lays particular emphasis o n the universally applicable procedures with orthoesters. Procedures for preparing spiroketals,
which are basic to a number of natural substances (cf.
F. Bohlmann et al., Chem. Ber. 94,3193 (1961)), may perhaps
be missed but they can be found later in a different connection
(pp. 552 and 699ff).
Angew. Chem. internat. Edit.
Vol. 7 (1968) J No. 2
-
~
~
Ketene acetals should also be included in a subsequent
edition; a single example only is referred to in the chapter
“Epoxides” (p. 484).
Under the subject “Conversions of oxonium salts” synthetic
methods involving pyrylium salts are mentioned briefly (pp.
352-358 and 363-365). On the other hand, acid- and basecatalyzed ring-opening reactions of epoxides are described
twice (p. 42ff. p. 448ff.). Perhaps this is inevitable in a work
written by several authors. Among the transformation reactions of epoxides, the preparatively interesting removal of
the oxygen atom by triphenylphosphine with the formation
of an olefin may deserve a comment. I n the treatment of the
methods of oxetane preparation by cycloaddition of olefins
to ketones (p. 503) there is no mention of the photochemical
formation of oxetanes (Paterno-Biichi reaction) from olefins
and carbonyl compounds; this method is of preparative
interest and in many cases proceeds stereospecifically. In
relation to the dihydrofuran-diene adducts (p. 559) in the
chapter o n the preparation of five-membered cyclic ethers,
some remarks concerning the stereochemistry of the adducts,
such as have been made in the case of similar compounds
on page 641, would be entirely appropriate.
Further, it would seem useful to the reviewer to adopt the
IUPAC nomenclature (pp. 559, 641, 643, 647), because
finding of the compounds discussed in collected works from
the subject index would then be made easier.
These few critical remarks are the only ones to have occurred
t o the reviewer during a careful reading, in which he was
assisted by Dr. H.-D. Scharf. In view of the abundance of the
material presented and discussed, this is proofof the qualityof
the work. The volume is a rich mine of chemical knowledge.
F. Korte
[NB 640 IE]
Biochemie der Vitamine (Biochemistry of the Vitamins). By
Th. Bersin. Akademische Verlagsgesellschaft, Frankfurt/
Main 1966. 1st Edit., vii, 296 pp., 16 figures, DM 44.-.
The author, who was compelled to undertake this venture by
his early work on the subject, attempts to describe the biochemical function and the therapeutic use of vitamins for the
benefit of physicians and dieticians. Such a work cannot be
more than a literature review, with more or less successful
attempts at systematization, and certainly cannot be original.
The book is divided into a general part, in which much of the
material is distorted though not actually incorrect, and a
special part, in which the various vitamins are discussed in an
old-established manner. A large quantity of material, divided
into biosynthesis, mode of action, therapeutic action, and
analogs, is compressed into a relatively small space, but
the discussion is frequently not sufficiently critical. In many
cases matters cannot be regarded in such a n unambiguous
and schematic way. It would indeed be delightful if they were
as certain as they appear to be from this presentation to the
uninitiated reader (e.g. in the methionine synthesis and the
mode of action of mercaptopurine). No definite function of
vitamin BIZ has been established in higher plants; the vitamins formed by intestinal bacteria are scarcely a source of
self-provision.
The unbalanced treatment of the material is a particularly
striking weakness. Trivia are given importance by a few
words (orbitals, nonpolar, translational motion); Americanisms (absorption instead of resorption) and nonstandard
units (yy, mcg) are simply adopted. Strange nomenclature
(isoalloxazinebenzopteridine,pyridoxaminium-5’-phosphate)
and interpretations (mongolism as mutation) seem dubious.
Apart from incorrect references ( Wolley, Jacobs, etc.) the
references to the authors own work (e.,q. Function of the nucleic acids: Vitalstoffe 8 (1963) 5) and the style are irritating.
On the other hand, the book contains a great deal of carefully
collected and useful material. The medical material will seem
interesting to the chemist and the chemical material to the
physician.
L. Juenicke
[NB 586 IE]
Angew. Chem. internat. Edit. / Vol. 7 (1968) / No. 2
Kurze Anleitung zur Berechnung von Tc-Elektronensystemen
(A Short Introduction to the Calculation of x-Electron
Systems). By J. D. Roberts. An extended translation of
“Notes o n Molecular Orbital Calculations” by F. Wille.
S . Hirzel-Verlag, Stuttgart 1966. 1st Edit., xi, 165 pp..
paperback, D M 19.80.
The “lecture notes” type of textbook, with its economic
presentation, whose availability up to recent times has been
unfortunately restricted predominantly to English-speaking
countries, is here available in an exemplary form. The
didactically sovereign, easily understandable, and sometimes
unorthodox manner, which follows that of the basic Roberts
lectures, including those given in Munich in 1962, introduces
the student to the Huckel molecular orbital theory (HMO)
as the simplest quantum-mechanical approximation procedure - “to be able to make MO calculations while swinging
in a hammock beside a mountain lake”. N o extensive mathematical knowledge is assumed, and numerous exercises
provide an opportunity of becoming familiar with quantities
such as charge and bonding order, free valence, and delocalization energies. Further chapters deal with the application to
aromatic, heteroatom-containing, or nonplanar electron
systems, and t o the prediction of chemical reactivities. In
conclusion, the quantities neglected by the H M O theory are
discussed critically. There is a n appendix consisting of
worked examples, two original publications, and a bibliography. The German text is lucid; the number of misprints
is tolerable (e.g. cis-butadiene (p. 5 5 ) is always treated as
linear in the H M O scheme without making additional assumptions, “>” on p. 93 should be “<”. The chapter dealing
with determinant factorization with the help of group theory
has been extended to the general case, although only twodigit symmetry elements are used. A successful introduction
to determinant algebra has been added as a further appendix.
Numerical solutions of all exercises and an introduction to
the use of the now available H M O tables would have been
equally desirable. The book, provided with a preface by
R . ffuisgen, can also be recommended to the beginner as a
simple introduction to H M O theory and its application to
H. Bock
[NB 638 IE]
organic compounds.
Techniques in Protein Chemistry. By J. Leggett Bailey. Elsevier Publishing Company, -&msterdam-London-New York
1967. 2nd Edit., xiv, 406 pp., 118 figures, 53 tables, Dfl.
55.-.
The very rapidly developing methodology of protein chemistry reached a comprehensive level a few years ago. Standard methods are now available for characterizing and purifying the proteins themselves and their degradation products.
In many cases these may have to be combined in different
ways or even modified, but when used together they generally
succeed in elucidating structure. Some of these procedures
may well be replaced by superior techniques, but this book
attempts to select several proved and particularly well developed methods. Moreover, it chooses procedures which
are applicable to research where purification o r sequence
analysis is only occasionally employed.
The limitation to reliable manipulative techniques such as
paper chromatography, ion-exchange chromatography, and
fingerprint procedures for amino acids and peptides, N- and
C-terminal sequence determination, column chromatography,
strip electrophoresis, dialysis, and molecular sieve separation
of proteins, splitting of disulfide bonds and sulfhydryl
determination in protein together with certain important
basic methods such as protein, nitrogen and tryptophan
determination, finds expression in a n arrangement hardly
changed from the first edition. The final chapter deals with
methods of synthesizing simple peptides such as the enzymologist selects as substrates.
New developments in this field account for the substantial
increase in size of the second edition. Here again J. L. Bailey
has succeeded in selecting successful and reliable new devel-
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