May 20, 1955
BOOKREVIEWS
2917
folic acid series is discussed separately and includes a resum6 critical expository treatment combined with the judicious care in presentation make this a reference work of unusual of the physiological actions of the substances, as well as of importance. possible biosynthetic routes. The size of the book may discourage some persons from In keeping with the tradition of this series, excellent bibliography, author and subject indexes are supplied, and attempting to delve into its contents, but actually of the 1384 pages less than 450 pages represent text since there are the physical appearance of the volume is of a high caliber. Chemists and biologists alike will welcome the volume as an over 900 pages of tables and 37 pages of index. The reviewer found the index useful for broad categories but not addition to their libraries. so helpful in locating specific compounds. So much of the RESEARCH DEPARTMENT information is tabular, however, that this would be exCIBAPHARMACEUTICAL PRODUCTS, INC. HANSHEPMANN pected. SUMMIT, KEW JERSEY A detailed chapter on preparation of Grignard reagents is followed by one on their constitution and dissociation, then one on some radical reactions of Grignard reagents, followed by eighteen chapters covering reactions with comHeterocyclic Compounds with Indole and Carbazole Systems. The Chemistry of Heterocyclic Compounds. pounds containing the various functional groups. Much of Volume VI11 . ARNOLDWEISSBERGER, Consulting Edi- this presentation, of course, is factual copy of published Western Kentucky State work, but the authors have been motivated throughout to tor. By WARDC. SUMPTER, College, Bowling Green, Ky., and F. M. MILLER,Uni- explain the observations in terms of modern theory and to versity of Maryland, Baltimore, Md. Interscience Pub- evaluate conflicting data in the light of their own experience. A few of the topics dealing with Grignard reactions which lishers, Inc., 250 Fifth Avenue, New York 1, h7.Y . 1954. 307 pp. 16 X 23.5 cm. Price, $10.00 single copy, are given this type of critical appraisal include the radical xii reactions, Grignard reagent enolate formation, a-halo ketone $9.00 subscription price. dehalogenation, the concept of a quasi &membered ring This book, dealing with indole and carbazole systems, con- transition state in many Grignard reactions, constitutional tains a review of the methods of synthesis of the simpler factors affecting order of addition, mechanisms of carboxylic compounds such as indole, carbazole, isatin, oxindole, isato- ester reactions, hindered alkyl esters, speculations on the gens and indoxyl, and an account of the properties and re- reaction mechanisms with acyl halides and acid anhydrides, actions of these compounds and their more complex derivaeffective migratory aptitudes in epoxide ring opening, and tives. A resume of the highly complex naturally-occurring reaction mechanisms with alkyl halides. indole derivatives also is included. The material is sysAlthough this book will be invaluable as a work of refertematically presented and the reader obtains a good idea of ence, it seems reasonable to predict that chemists, intending the methods of preparation and the reactions of the indolic to use it only for reference purposes, will find themselves type of compounds although, as the authors mention, they staying to read it long after the reference is located. It is have not attempted to duplicate Beilstein in listing every that kind of book. compound. The chapter on indigo, for instance, does UNIVERSITY not delve a t length into the details, yet it supplies an over- SORTHWESTERS D . HURD EVANSTOX, ILLIPI’OIS CHARLES all picture of the problem a t hand and the way it was solved. I t is stated in the preface that the literature up to the end of 1952 has been consulted and that several important papers of 1953 have been included. Some omissions such as the structure of corynantheine, based on work published in Solvents and Allied Substances Manual with Solubility 1950-1952, and the latest structure of alstonine, published Chart. Compiled and edited by C. MARSDES,B.Sc., in 1952, lead one to the conclusion, however, that the literaA.R.I.C., British Industrial Solvents, A Division of The ture survey for 1950-1952 a t least has not been too thorough. Distillers Company Limited. Elsevier Press, 402 Lovett Furthermore, under the heading tryptophan, one would 429 pp. Boulevard, Houston, Texas. 1954. xii have expected to find some mention of kynurenine, and the 16.5 X 25 cm. Price, $12.95. biochemical relationship of these two substances. It is also The author states in the preface that he “has necessarily regrettable that the book is marred by numerous typoaccumulated a mass of information on solvents and allied graphical errors that careful proof-reading would have chemicals currently in commercial production. . . . A careavoided. Not to end on a discordant note, however, the book ful and critical study of this conflicting data has been made and the outcome is offered in this volume. That all the inshould be very helpful to the chemist in supplying him with formation contained in it should be completely accurate is a bird’s-eye view of a most complex field of organic chemistry too much to hope but the more serious discrepancies and and biochemistry in which research in recent years has been variations in published information and figures have been most active. eliminated by careful selection in an effort to ensure that DIVISIONOF PURECHEMISTRY the data here presented are as accurate as possible in terms of SATIONAL RESEARCH COUNCIL LEOMARION present knowledge.” OTTAWA, CANADA In a typical example of one of the more common solvents, such as acetone, where naturally fairly complete information was available, the following data are given. Under physiGrignard Reactions of Nonmetallic Substances. By M. S. cal characteristics and properties are listed: mol. wt., b.p., m.p., flash point (closed and open cup), auto-ignition temKHARASCH, Professor of Chemistry, The University of Chicago, and Otto Reinmuth, Research Associate, The perature, specific gravity, refractive index a t 20 and a t 25”, caloric value, specific heat a t 20°, coefficient of cubic exUniversity of Chicago. Prentice-Hall, Inc., Publishers, pansion a t 20” and the mean from 0-loo”, electrical con70 Fifth Avenue, hTew York 11, N. Y . 1954. xxii ductivity a t Z O O , dielectric constant a t 20”, explosive mix1384 pp. 15 X 23 cm. Price, $15.00. tures with air a t 20” (upper and lower limits), latent heat of Someone‘pnce remarked that if a speaker a t a gathering evaporation, latent heat of fusion, evaporation rate (for would ask Is there an economist in the house?” positive ether = 1 and for n-butyl acetate = loo), dilution ratios replies would come not only from the few followers of Adam for cellulose nitrate solutions for water, toluene, xylene, Smith who might be present but also from bankers, mer- petroleum naphtha and butanol, viscosity, surface tension chants, brokers and industrialists. Similarly, a question a t 20” and a t 30”, vapor pressure, solubility in water, critiput to a group of chemists “Is there someone here who cal temperature, critical pressure and critical density. knows about Grignard reactions?” might elicit almost uni- Other information given relates to methods of manufacture, versal response, for who among us has not carried out a industrial grades, azeotropes, physiological properties, and Grignard reaction? If pinned down, however, few of us storage and handling. The main manufacturers both in would care to be quizzed on the large area covered by the United States and i n Britain are given for each solvent. Kharasch antl Reininuth. The fact that no modern comIn other instances, p?rticularly for very special proprieprehensive treatise is available on a subjrct a? comrnoii as tary solvents, comparatively very few data are given. For this is testimony to the tremendous literature on the sub- example, under “Ttitrasolvan E,” a product whose manuject. The authors would have performed a valuable servicp facture is confined to Britain, only four physical rhnrzcterif they had prepared nothing but a bibliography, but the istics are listed together with storage antl handling.
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