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Book Review Handbook of Chemistry and Physics. Edited by C. D. Hodgman R. C. Weast and S. M. Selby

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The conversion of aromatic aldehydes into alkyl aryl ketones
has been achieved by K . D . Berlin, B. S . Rathore, and M . Peterson. When the 1,3-dioxolanes ( 1 ) obtained from the
aldehydes by condensation with ethylene glycol are treated
at 60°C under nitrogen with an excess of alkyl-lithium
(molar ratio about 1 :3) in cyclohexane/ether, the ketone
derivatives (2) are obtained via several intermediates ;
(a) A r = C&5,
(b) A r = p-CH3CsH4,
( c ) A r = p-CH30C&,
(d) A r = p-CHsC&14,
R = C4H9
R = C6H11
R = C4H9
R = C4H9
(87,5%)
(66,5%)
(787”)
(80%)
conditions, copolymers with irregular monomer sequences,
block copolymers, or copolymers with alternating structures
can be produced. The softening points depend on the composition: 168-174’C for a polymer with little dimethylketene and 150-155 “C for one containing 10 % dimethylketene. The rate of decomposition at temperatures above
220 “C lies between that of the acetylated homopolymer and
that of the trioxane copolymer, which is more stable than
( I ) . / European Polymer J. I , 25 (1965) / -HI.
[Rd 323/532 IE]
A cycloaddition of diphenylcyclopropenoneonto aminoalkenes
has been observed by J. Ciubattoni and G. A . Berchtold. 1Diethylamino-l,3-butadiene(2) and diphenylcyclopropenone
( I ) react in refluxing benzene to form 2,7-diphenyltropone (3)
as yellow platelets, m.p. 132-133 OC, in 68 %yield. Similarly,
( I ) and 2-(N-pyrrolidino)-3,4-dihydronaphthalene(4) afford
2,9-diphenyl-8-(N-pyrrolidino)benzo[d]cyclonona-2,4,8-trien1-one (5), m.p. 136-137OC, in 6 2 % yield. The reaction
involves 1,2- and 1,4-additions, but it is still unknown
hydrolysis of (2) affords the ketones (3) in yields of 66.5 to
80 %, together with equivalent amounts of alkane and ethylene. / J. org. Chemistry 30, 226 (1965) / -Bi. [Rd 300/509 IE]
A new thermostable copolymer of formaldehyde ( I ) is desibed by G. Natta, G. F. Pregaglia, G. Mazzanti, V. Zamboni,
and M . Binaghi. It is produced by copolymerization of HCHO
with dimethylketene catalysed by tertiary amines. The.
amount of dimethylketene incorporated depends largely
upon the polymerization temperature: 80 % is built in at
0 “C and progressively lesser amounts at higher temperatures,
where side reactions also occur. By varying the reaction
whether its mechanism is a one-step cycloaddition or a
Michael addition with subsequent cyclization. / J. Amer.
[Rd 331/540 IE]
chem. SOC.87, 1404 (1965) / -Ma.
BOOK REVIEWS
Carbene Chemistry. By W. Kirmse, in collaboration with
H . M . Frey, P. P . Gaspar, and G . S. Hammond. Organic
Chemistry, a Series of Monographs, edited by A . T. Blomquist. Academic Press, New-York-London 1964. 1st edit.,
VIII + 302 pp., numerous tables, several illustrs., linen
$ 9.50.
Prolific developments have taken place in the field of carbene
chemistry over the past ten years. Hundreds of publications
have appeared, and anyone not working in this field could
hardly have read even only the most important of these. The
appearance of this monograph - incidentally the first in the
series “Organic Chemistry” edited by A . 7’. Blomqwist - is
therefore highly welcome.
The book deals mainly with the reactions of carbenes and
their mechanistic aspects. Following a short introduction,
there are nine short but pregnant chapters of the nature of
review articles which give a practically flawless survey of the
preparation, reactivities, and preparative applications of all
the carbenes known to date. There is a carefully compiled
bibliography covering literature sometimes until the start of
1964. A welcome feature of the book is that topics on the
fringe of carbene chemistry are also dealt with, e.g. the
synthesis of diazirines or the preparatively important cornpounds chloromethylzinc and iodomethylzinc,which although
not true carbenes, behave as if they were.
Two chapters by competent authors examine theoretical
aspects of the subject. In one, H . M . Frey relates why it must
be assumed that methylene made by photolysis or thermolysis
from diazomethane or ketene has excess translational and/or
Angew. Cliem. internat. Edit. / Vol. 4 (1965) 1 No. 9
vibrationaI energy. In the other, P. P. Gaspar and G. S.
Hammond discuss the spin state of carbenes. Here, among
other things, the chemist is carefully shown the pitfalls into
which he can stumble if he attempts to deduce the electronic
state of a carbene from its chemical reactions.
The reviewer found this book a pleasure to read. Since he
is convinced that any other scientist interested in the chemistry of short-lived intermediates will enjoy the same experience, he can recommend the book most highly. It is
unfortunate that monographs on modern trends become
outdated rather rapidly. It would therefore be a commendable
undertaking for the author and publisher to produce a
translation into German of the work with inclusion of any
new material that has appeared.
U.Schollkopf [NB 3941252 IE]
Handbook of Chemistry and Physics. Edited by C. D . Hodgman, R. C . Weust, and S . M . Selby. A Ready-Reference
Book of Chemical and Physical Data. The Chemical
Rubber Company, Cleveland, Ohio, U.S.A., 1964. 45th
edit., XXI -F 1472 pp., imitation leather, about $ IS.-.
The fact that a reference book has appeared in 45 editions in
45 years is an outstanding proof of its quality, which cannot
be diminished or augmented by any review. However, the
45th edition of the “Handbook of Chemistry and Physics”
has undergone so many changes in comparison with its
predecessors that some appraisal seems justified.
The format of the book has been doubled; this agreeable
feature makes the volume handier and easier to peruse.
795
The sections of the book of greatest interest to chemists have
been reorganized. There is a section on “Elements and Inorganic Compounds”, another on “Organic Compounds”,
and a section with data which are of general interest to
chemists, including for example, a list of over seven
hundred azeotropic mixtures (new), dissociation constants,
specific heats and enthalpies of some metals a t low temperatures (new), vapor pressures of organic and inorganic
compounds, etc.
The table of the “Physical Constants of Organic Compounds”
(525 pp.) is the most extensive. Here data are listed for over
13500 substances, separate columns being devoted for each
to the name, formula, synonyms, molecular weight, crystal
form, color and specific rotation, melting point, boiling
point, density, index of refraction, solubility in water,
alcohol, ether, acetone, benzene, and other solvents, and a
literature reference. This table has been extended by about
5000 entries in this edition, and is probably the largest of
its kind anywhere.
It would take too long to characterize the variety and
abundance of the other tables of chemical, physical, and
mathematical content in turn. However, it may be mentioned
here that a newly revised table of all known stable and
radioactive isotopes is given, that the physical properties
of inorganic compounds are given as fully as those of organic
substances, and that a short portion of text is devoted to
each element - a n unusual feature for a handbook - describing its properties, discovery, occurrence, and chemical
behavior. The reviewer would find it hard to pose a question
within the scope of this book which it would fail to answer.
A few items could be improved in later editions. The table
on buffers is too short and does not d o justice t o the importance of these solutions - especially in biochemistry. The
section on the nomenclature of organic compounds contains
the IUPAC rules of 1957 and a list of carbocyclic and heterocyclic rings. The reviewer considers this to be insufficient,
even though the long table on the physical properties of
organic compounds that follows alleviates this situation a
little by giving examples. It might be worthwhile to include a short introduction to the nomenclature of functional
organic compounds and derivatives. The structural formulae
in the large table (particularly on p. C-75) are neither attractive nor clear; in the formula of coniferyl alcohol o n p.
C-259, the positions of OCH3 and OH have been interchanged; sometimes, e.g. with steroids, one has difficulty in
recognizing the compounds portrayed. Here there is definitely room for improvement ; the structural formulae
should be set by a printer who has the necessary type available. Uniform use of the designations D, L, d, 1, (-), and (+)
would also be preferred. H . Griinewald
[NB 3951253 IE]
Organic Experiments. By L. F. Fieser. D. S. Heath and Co.,
Boston 1964. 1st edit., 325 pp., numerous figs., linen
about .t 7.00.
The main aim of this new book by Louis F. Firser is the
experimental training of students.
Practical experiments, described in every detail, form the
mainstay of the book. In addition, particular emphasis is
placed upon the identification and characterization of the
compounds prepared using chemical and physicochemical
methods. Less attention is intentionally paid to reaction
mechanisms.
The book starts with descriptions of the equipment required
for preparative work in organic chemistry. This is followed
by an introduction to elementary practical techniques such
as the handling of wash bottles: filter flasks, suction filters,
and burners, distillation, crystallization, extraction, ere.
Even during this introduction to practical techniques exercises are given, e.g. the isolation of citral from lemon grass
oil during the discussion of steam distillation. In the course
of the practical preparations that follow, any new apparatus
796
or methods that are required for the synthesis or separation
of the compounds to be made are described separately ( e . g .
chromatography).
There are no old-fashioned, hackneyed procedures, e. g. that
for the preparation of bromobenzene, included among the
selection of examples and instructions given; instead,
interesting preparative work applying the most modern
methods is described. For example, directions are given for
the synthesis of diacetylene, on how to reduce double bonds
with NaBH4 o r HCI/Pt, for the preparation of hydrazobenzene from azobenzene with diimine, the addition of dichlorocarbene onto cis,cis-l,5-cyclooctadiene,the synthesis
of tropylium bromide, and the production of trypticene via
dehydrobenzene. Even a n enzymatic reaction has been incorporated, viz. the isolation of L-alanine from the racemate
of the acetyl derivative, as well as analysis of peptides by
chromatography.
In order to introduce the student to the applications of
spectroscopic methods, there is a chapter on 1,Zdiphenylethane derivatives, which skilfully and instructively combines
preparative and spectroscopic methods.
An interesting feature is a chapter on the calculation of
costs, for the attention of the student should occasionally
be called to such matters too.
The subject matter in each individual chapter is presented
with extraordinary clarity; on the margins there are keywords and suggestions and even warnings whenever a
reaction could become dangerous. Practical exercises are
added at the ends of some chapters. It must be said that
every chapter is a success. However, there is no continuous
didactic development from chapter to chapter such as i s
normally encountered in practical textbooks of organic
chemistry. It is therefore up to demonstrator or supervisor who will himself find many instructive exercises in the book to select a series of preparations to be carried out by the
student.
Fieser’s “Organic Experiments” should definitely be present
in every organic undergraduate laboratory.
[NB 407/265 IE]
H.-J. Bestmann
Physikalische Chemie (Physical Chemistry). By Klaus Sclzu.fer. Ein Vorlesungskurs (A Lecture Course). SpringerVerlag, Berlin-Gottingen-Heidelberg-NewYork 1964. 2nd
432 pp., 81 figs.,
improved and extended edition, XI1
linen D M 36.- (about $ 9.00).
+
The alterations introduced in this new edition of Schufer’s
book [*I affect mainly the chapter on the structure of matter,
which has been extended and modernized.
The book is divided up as follows: I. States of aggregation
and their equations of state (46 pp.); 11. Energy content of
matter (55 pp.); 111. Chemical and thermodynamic equilibria
(91 pp.); IV. Electrochemistry (49 pp.); V. Chemical
kinetics (21 pp.); and VI. The structure of matter (148 pp.).
The book closes with two tables and a subject index. There
is no need for an author index since there is only one reference
given in the whole book.
In its structure and organization, the book is closely allied
to the textbooks by Eucken, to which Schafer did of course
make many contributions. However, a novel feature of this
work is the detailed treatment given to the fundamentals of
quantum mechanics and to the theory of the chemical bond.
Here the discussion goes into the most recent developments,
whereas thermodynamics and electrochemistry, for instance,
are dealt with in the conventional way. Kinetics receives only
brief treatment on 21 pages, and interfacial phenomena are
only briefly touched upon.
The presentation and appearance of the book are attractive.
R. Haase
[NB 389/247 IE]
[*] Cf. Chemie-1ng.-Techn. 24, 471 (1952).
Angew. Chem. internat. Edit. 1 Vol. 4 (1965) 1 No. 9
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