Some modern methods of organic synthesis - ACS Publications

Synthesis. Editor W Carruthers, Cambridge Uni- ... graduate students, faculty, and synthetic chemists .... rhrm~wl pnlceiwi drm(m1r~CPs that the law. ...
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book reviews ignored. This text does not seem well suited for use where chemical calculations are of interest. Donald D. Marshall Sonoma Slate University Sonoma. CA 95476 Catalyfic Hydrogenation In Organic Synthesis Procedures and Commentary

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This is a succinct, business-like lahoratory handhook dealing with heterogeneous catalytic hydrogenations of organic compounds. The emphasis is experimental and practical, with the subject presented asaseries of tested procedures for different types of hydrogenations. The coverage is selective; the determining factor in including a reaction is its usefulness in exemplifying the class under consideration. There is no attempt made to provide an exhaustivecoverage or to include only recently published material. After an eight-page introductory chapter, which discusses some practical and eeneral aspects of hydrogenation, the book goes directlv of orennic comoounds . ~to the ~reduction ~ ~ ,n~~~~~~ arranged according to the functional group. Dit'ferent chapters take up hydrogenation of acetylenes, olefins, nitroso groups, nitriles, oximes, imines and C=N bonds, aldehydes and ketones, aromatics, and sulfur eompounds. In addition, two chapters cover reductive amination and alkylamination of c:arbonyls. A separate chapter discusses hydrr,genolysis. Each chapter includes some hrief, pertinent comments on general aspects of the reduction type. Systematic attention is devoted to selective hydrogenation of one functinn in the presence of another. No treatment of the catalytic hydrogenatin" of esters or amides appears, presumably hecause alternate methods are oerferred or ~~~~~~~

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organosulfur and selenium compounds completes the new categories. Considerahle selectivity has been exercised in the deletion of material and the author's hope ". ..without detriment to the usefulnessof the honk" Is st~c~c.sifully rralined. T h r prmripal advantages uf the t ~ x t h w k nrr two. Firit, thcrtcrllcnt organizationand ielevtivity pruvidr* w r y rlvar $often outstanding) rxamplr 11, lllustratr not only the principal \ , a l u ~of and limitations 181 the method but also a qualitative comparison with other methods. The approach is very much interpretative rather than exhaustive. Second, the writing style is first-rate, and the text is satisfyingly free of typographical errors. Thus, upper level undergraduates, graduate students, faculty, and synthetic chemists will learn more easily and use the wealth of information provided. On the less appealing side, the most recent references (exceot one) are for 1976. Although thrlr H W ~UIIIPI.~US, ihc unfortunntr delay in prmrmg rendrrr thr irxthuuk lecs valuable than i t might he. .An additi~nnlfeature of some concern is the relative scarcity of references to reviews. Moreover, the style of listing references which might have obviated the need for an author index is certainly a shortcoming. It is not possible to start from the reference (or author) and locate the material. While the direction from material to reference (or author) is clearly a major use the reverse is often valuable and desired. Finally, the paperback price is reasonable fnr a textbook, however, the hardcover price is very expensive. Shellon Bank ~

Editor Morris Freifelder, John Wiley & Sons, New Yark, 1978, Figs. & tables. 23% X 16 em. xvi 191 pp. $18.50.

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has been deleted to preserve conciseness, and importantly, the crisp, clear writing has been, if anything, improved. The format, chapter headings, and emphasis are the same as the first edition. Notable major additions include applications of oreanmilicon eamoounds in svnthesis. novel

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S a l e univers,ty of New York at Albany Albany. NY 12222

Transltlon Metal Organometallics in Organic Synthesis. Vol. II genations inti a small, handy r e f e k e work. The hook will be useful to those faced with the task of performing a catalytic hydrogenation or of planning a synthesis involving Walter J. Gensler Boston University Charles River Campus Boston. MA 02215

Some Modern Methods of Organic Synthesis Editor W Carruthers, Cambridge University Press, Cambridge, 1978. Figs. & tahles. 22 X 13.5 cm. xi 532 pp. Paperhack 815.95, Hardcover $59.50.

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This is a welcome second edition to the well-written textbook hy Carruthers (1971). New material has heen added, some material A288 / Journal of Chemical Education

Editor Howard Alper, Academic Press, New York, 1978. Figs. &tables. 23.5 X 16 cm. v 188 pp. $19.00.

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Folluwing in the style of Vnlume I of this two-volume work, this short book (163 pp. of text and references) also reads like Annual Reports, hut is more highly illustrated. Unlike Volume I, Volume I1 is relatively free of errors; I detected nnly a few typographical errors, and there is a t least one arrow drawn in the wrong direction. Chapter 1, by Nicholas, Nestle, and Seyferth, deals with the potential utility of transition metal-alkyne complexes and d e ~ rived cluster compounds as reagents in organicsynthesis. I t isvery wellogranized and loaded with information, as are all three chapters. The presentation flows logically fkmi one subject to the next. After. a short discussion of the handing, structure, and

preparation of metal-alkyne complexes, the bulk of the chapter deals with various reactions of alkyne complexes and the synthesis and reactions of alkylidynetricobalt nonacarbonyl complexes. Chapter 2, by G. Jaouen, discusses arene complexes in organic synthesis. Much of this section deals with reactions on arene rings as influenced by the chromium tricarbonyl group. Other subjects include stereoehemical consequences of the transition metal camplexation of an arene, and orthometallated arenes. The final section of this chapter deals with catalytic properties of a& comolexes. The chanter hv H. Aloer is the shortest of .~~. .~~~~ ~, ~~~-~ the three hut the most diverse. The author has done 'an admirable job of tying together topics such as oxidation, reduction, addition, eliminatjon, cleavage, and rearrangement processes. A large variety of organotransition metal complexes are included in this chapter. The main discussion in all three chanters

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appeared on a topic appropriate to these chapters, the subject is dismissed and a reference to the review given. On the other hand, references on topicioften go back ten years or a,in order to present a complete picture of the subiect. Publications as recent as earlv I T 8 arc included i n tne rhaprrrs. Thir hwk cwrsinsn wealth 1 4 mfmnstim and should be valuable as a reference book to researchers interested in the field of organometallics in organic synthesis. ~

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Michael F. Farona

me University of Akron Akron. OH 44325

Principles of lnaustrial Chemistry

Chris A. Clausen 111,Guy Mattson, John Wiley & Sons, Inc., Somerset, 1978. Figs. & tables. 23 X 16 cm. vii 412 pp. $18.95.

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The authors, who have had industrial as well as academic experience, recognize the need to better prepare students for a career in industry. "Difficulties arise in the application nf principles to specific, practical problems; in a poor understanding of some very hasic engineering concepts, and in a lack nf awareness of what the chemical industry is, how it operates, and how thechemist fits intn the scheme." The authors' purpose in writing this book "is to supplement or complement the traditional training of s chemist in order to help him through the change from the academic to the industrial world." The book is intended as a senior or graduate level course or as a personal reference guide and focuses on the general theme of pmcess development. The individual chapters are devoted to pertinent topics in harmony with this theme. What the chemical industry is and what it does. Basic considerations to envision the process are presented. Material aceauntine- .lindustrinl stoichiomel r ) I shle*rs the o p w a l ~ m(11 the Ian, of r w w r w t i m irf ma% E n ~ r g garrounrms m r h r m ~ w pnlceiwi l drm(m1r~CPsthat the law (('mtinued on page A290)