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PROGRESS IN ORGANIC CHEMISTRY. VOLUME 2
Edited by J. W.Cook, Regius Professor of Chemistry. University of of University London. demic Press, Inc., New York, 1953. 212 PP. 16 X 25.5 cm. $7. Tnrs is the second volume edited by 3. W. Cook of an apparently continuing series on "Progress in Organic Chemistry." The first volume appesred in 1952 (3. &EM. Eouc., 29, 639 (1952)) and the second volume follows the previously established pattern.
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The articles are concise rather than comprehensive and are of the same type as are to he found in Chemical Revinus. In each ease the reviewer is a recognized on the of his ohap ter and one who has played an active part in its advancement. ~h~ six chapters discussed in the present volume and their reviewers are: "Some recent developments in theoretical organic chemistry," M. 3. 5. Dewar; "Organic fluorine compounds," M. Stacey; "The chemistry of the triterpenoids," D. H. R. Barton; "The partial synthesis of cortisone and related compounds from accessible steroids," F.5.Spring; "The relation-
SEPTEMBER,1954 lustcad, auJ in keeping with the I s & erctngemcnt I,! the book according to cla3n of compuund, I . P., to functi~~mlity, vsrious aspects of ~tercochcmiatryarc de\.tlupe.l only wllcrl vompounds calling for such development are encountered. For example, geometric isomerism is discussed briefly under olefins. The asymmetric carbon atom, optical activity, resolution (note that the wo?k of Schlenk and of Powell on resolution by formation of inclusion complexes is presented), asymmetric induction, etc., are discussed in the section on alcohols after coming to "active" amyl alcohol. Asymmetry around nitrogen is presented under properties of smiues. The Beeyer strain theory is found under glycols in connection with the stability of ring ethers. Restricted rotation is introduced in the section on compounds related to biphenyl. Stereochemical problems related to cyclopropane and cyclohexane are disoussed briefly in the respective sections. Very little is done with the idea of conformation. The Walden L A. GOLDBLATT inversion is introduced quite properly under the interconversions UNTTED STATEBDEPARTMENT OF A ~ R I C U L T U R E of a-amino acids. But the topic of nucleophilic substitution at a NEWORGE*N., LOO.SI*N* saturated carbon is disposed of in one-half page of fine print as a subtopic under the inversions of a-amino acids. The subject of stereochemistry outs across all of organic chemistry. As far as this reviewer is concerned, stereochemistry 0 LEHRBUCH DER ORGANISCHEN CHEMIE should be accorded the space and attention it deserves as a major topic inits own right. Paul Karrer, Pmfessor at the University of Zurich. Twelfth The book is carefully indexed, 56 pages of three-column entries edition. George Thieme Verlag, Stuttgart, 1954. ur 949 pp. being occupied by the index. The detailed Table of Contents 6 figs. 1 table. 20 X 27 cm. $14.20. (12 pages) is likewise very useful in locating material. No speP ~ o ~ ~ s s o ~ P ~ u ~ K ~ ~ ~ ~ ~ ' s " L e ~ b u ~ h d e r ~ r g a n i s ccific h e nreferences C h e m i e ,are " given in the text. However, the practice is which first appeared in 1925, has gone through many editions. followed of mentioning pertinent names parenthetically. Also This. the twelfth and latest edition. aims to nresent a omnorehen- frequent references are made to books, treatises, and monohe literature graphs. sive bnd up-to-date account of org&ic chemistry. The inclusion of such a large amount of material in one volume coverage goes to early 1953. A check showed that recent developments in the chemistry of such compounds as aureomycin, ce- is made possible by presenting many sections in fine print. The drene, sterculic acid, caryophyllene, coenzyme A, and metal readability is not impaired by this device. The paper, printing, hicyclopentadienyl "sandwiches" are included. The work of and binding are excellent. Typographical errors are preotieally in Bijvoet on absolute configuration of tartaric acid is given. The nonexistent. The book is massive not onlv in seooe h u t also --treatment is especially thorough in the natural products areas. siae. I t has oversiee pages and weighs almost 5 pounds. It is The emphasis on alkaloids and on heterocyclics is noteworthy. not oonveniently held on thelap. The great virtue of the "Lehrbuch" is that it presents in a sinThus, while other texts of a comprtrable nature devote less than gle v ~ l ~ nill) t . up-t~-cl?tleand cysrernltic array of facts x1,out. 5 ner cent of their naee ,. soace to alkaloids and heteraovclics. the " L h b u r h " dcvotcs no lcvt thuu 15 per crut to tllrtn. A ahort organic ctwmistry. This iu rhr ~ t i t c diutcnLof l'n,frisor iinrrur, chnptcrdtding with icoroprs in organic compouud? is iufornl~tivc and in this hc Ins sucrrrded ndmirnhlv. liur Iwswer n~clcomc the facts, many organic chemists wiil rue the de-emphasis of and welcome. Although in general the author's presentation leaves little room theory and of reaction mechanism. Within Professor Karrer's for disagreement, some points to which exception is taken might working frame of reference and the confines of a single volume be mentioned. For example, the formation of 1-bromo3chloro- the de-emphasis probably is unavoidable. However, this reDroDane by addition of hydrozen bromide to ally1 chloride, a reac- viewer suggests that a better balance between description and tion comionly accepted as ifree radical priceas, is given on interpretation-obviously a t the expense of the former-would page 50 presumably as an ionic process, with the inductive effect make the "Lehrbuch" an even more popular treatise than it is .. of the chloromethyl group reversing the Markovnikoff addition. "nw Potential purrhnscrs of the "Lrlrhurh" should renlirc t . h ~ an t On page 269 the reader is left with the impression that, in the Claisen condensation of ethyl acetate, something other than Englieh trmslntion is avaihblc (ioul.th E n g l ~ hedition, Elsevirr neutral acetoacetate is the precursor of sodioacetoacetate. The Prr.s. 1950). and also that rhna h r r beerr announced for i,ul,l~Pummerer mechanism (page 273) for the acid-catdy~edconver- catioh of t h i English edition in two volumes (Elsevier ~ r e s s j . sion of hydroxymethylfurfurd to levulinic acid has little to comWALTER J. GENSLER mend it. There is no real need to involve the hydrated aldehyde form as an intermediate in the mutarotation of gluoose (page 324). The perhenzoic conversion of olefins to epoxides is a reaction of perbenzoic acid and not of its sodium salt (page 511). Linoleic and linolenic acid, although necessary food factors for the rat, have not been shown to be essential for normal growth in man GENERAL COLLEGE CHEMISTRY (page 211). Tho description of quinoline as a weak base (page 0 783) is suitable, hut the statement that isaquinoline is rt "ziemheh M. Cannon Sneed, I. Lewis Moynord, and Robert C. Bmsted, starke" base (page 788) is not appropriate. Both compounds University of Minnesota. Second edition. D. Van Nostrand Co., (Ka's3.2 X 10Fo and 2 X lo1, respectively) are generally de- Inc., New Yark, 1954. vi 693 pp. 16.5 X 23.5 cm. $6.50. scribed as weak bases, certainly so in comparison with.ammonia. Finallv, the 1951Roberts-Chambers svnthesis of cvclooronanolbv THISsecond edition of a well known text certainly meets and perhaps exceeds the standard set by the first edition ten years ago. Its outstanding characteristic is clarity of expression. Too .-.,. often, the textbook author writes as though he senses a fellow A criticism mare serious than any of the above-mentioned con- teacher looking over his shoulder with s. critical eye. Here, the cerns the manner of dealing with stereoehemistry. No one sec- authors seem to he seated around a tutorial table with a sroup of tion is devoted specifically to stereochemistry as a general subject. inquisitive young students; their remarks are addressed t o these
ship of natural steroids to carcinogenic aromatic compounds," H. H. Inhoffen; "Some recent developments in pyridine chemistry," J. P. Wibaut. The average organic chemist will find the first chapter quite difficult to digest but should have no particular difficulty with the other chapters. The treatments are adequate and well organized. An ittempt has been made to bring the literature references more nearly up to date than was the case in the fist volume. Each chapter has a number of citations to the Literature subsequent to 1950 but an abnormd proportion of these are to the authors' awn publicstions. The extreme example is that of the fifth ohapter wherein five out of 84 references are to publications since 1950 hut all of these are to theauthor's own work! As in the case of the first volume the typography is good but the price seems high.
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