topics covered in earlier hooks of similar titles by Ginsberg, Lloyd, and Snyder, let that fear he dispelled. The first apparent difference is that the usual first chapter a n the "concept of aromaticity" has been tastefully omitted. Next we find that the subject matter is, on the whole, quite different. There are 11 chapters, each written by a specialist in the particular area: heteronins (Anastassiou). heotsfulvenes (Bertelli), dihydropyrenes (Boekelheid), &lopentadienyl cations (Bredow), systems containing 4-membered rings (Garratt), monocyclic lor-electron systems (KempJones and Masamune), the phenalenyl system (Murate), snnulenes containing chmulenie and acetylenic linkages (Nakagawa), uranoeene (Streitwieser). oerturbedll2lan-
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of authors is excellent and the small amount of bickering over "who did what first" only serves t o convince the reader that the authors themselves really are involved in whatever i t is. In general the writing is clear and in the style found in Accounts of Chemieol Research. In spots the printing leaves something to be desired as some pages are significantly darker than orhem and all of the drawings are mmiarurired. Rut ahat can one exwrt for $21.50?!! With regard t o the qukstian of currentness, the copyright date is 1973 and over half of the chapters include references from that year. For this the editors are t o he congratulated. Although a considerable portion of the material covered in this hook has appeared in the form of review artides (notahly the chapters by Anastassiou and by Kemp-Jones and Masamune), this hook, and probably the remainder of the series, belongs in all chemical libraries. The worker in the field of nonbenzenoid aromatic chemistry will buy i t without urging and the nonspecialist really does not need a personal copy. Thomas J. Barton bwa State University Ames, Iowa 50010
Sulfur Ylldes. Emerglng Synthetic Intermedlates
Barry M Trost and Lawrence S. Meluin, University of Wisconsin. Academic Press, New York, 1975. x 344 pp. Figs. and tables. 23.5 X 16 cm. $39.50.
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of epoaides from carhonyl compounds, cyclopropanes from Michael-type carhon-carban double bonds, and homoallylie sulfides via sigmatropic rearrangement. As in the case of the ylide preparations, the formation of three-memhered rings is categorized according t o the nature of the ylide. These include "methylide," "alkylide" and "stabilized ylide" processes. A brief but useful comparative evaluation of alternative synthetic methods leading t o the major reaction products of ylides is provided. Next, in a very useful complement for those interested in auulvine.. the chemical reactions, 27 experimental pmcedurer relared 1 . 0 sulfonium inl~.r, ylidcr, ep. oxides, ryclopropanes, and rearrangement .produck are provided. Approximately one-half of the hook ronsists of s com~rehenuivetabular disulav of examples in dhieh the three kinds ajp&tinent reactions have been applied. The style of presentation, whieh is similar t o that in "Organic Reactions," includes starting materials and products (name or structure), reaction conditions, yields, and references. The topics are: (1) Epoxidations with Methylides: Ketones; (2) Epoxidations with Methylides: Aldehydes; (3) Epoxidations with Substituted Ylides: (.4 ) Cvelo, prupanatwn with Methylides: r S ) Cyclopropanations with Substituted Ylides: 16) Rearrangements: [2,3]Sigmatropie; and (7) Rearrangements: 1.2-Shift or Stevens
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For the moat part the three types of applications of reactions of sulfur ylides were first looked a t extensively in the late 1960's. Books predating this period do not present too much overlap in synthetic chemistry, although the synthesis of epoxides from ylides is thoroughly covered through January, 1966 [Johnson, A. William, "Ylide Chemistry," Academic Press, Inc., New York, 1966, pp. 3063661. The greatest overlap of information for synthetic application probably appears in "Modern Synthetic Reactions" [House, H. O., "Modern Synthetic Reactions," W. A. Benjamin, Inc., Menlo Park, California, 2nd Ed., 1972, pp. 709-7331, whieh deals with ylide sources, epoxide formation, and cyclopropanation in a much more limited sense.
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The monograph on sulfur ylides was written primarily for the use of synthetic organic chemists, hut with a supplementary general, non-comprehensive treatment of the structural and mechanistic aspects of the subject. According t o the authors, i t is for those "who must face the prohlem of constructing molecules" and it is intended "to stimulate new research in this exciting area." The scope, approach, and style serve this purpose well. The formation of new carhon-carbon bonds through the use of the ylides (r-sulfuranes) most nearly describes the goal of the presentation. The authors describe the synthesis of sulfonium salts and their analogous ylides, with efnphasis on the so-called stabilized (e.g., with adjacent carhonyl groups) and
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unstahilized forms. Suhseouentlv. the use of t h e x ylides is deacrrhed in the formallon
George K. Helmhmp univwsity of Califmia Riverride, Califwnia 92502
Natural Products Chemistry. Volume 1 Edited by Koji Nakonishi, Toshio Goto, Sho Zto, Shimaku Natori, and Shigea Nozoe. Academic Press, Ine., New York, 1974. x 562 p. Figs. and tahles. 19 X 26 em. $32.
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Volume 1covers the structure, synthesis, and hiosynthesis of terpenes and steroids. The stated intent of the series is t o fill the gap between the organic chemistry texthooks and the comprehensive treatise, and the intended audience consists of both the specialist and non-specialist. (Continued on page A2761 Volume 53.Number 5, May 1976 / A275
book reviews 'I'he most notable feature of this series is the emphnris on rapid visual retrieval of Information, and nearly three quarters of the hook is occupied by schematic diagrams, which allow the reader to grasp the essence of each topic with a minimal amount of effort. The chapter headings are 1) Classifiestion of natural products (consisting mainly of a seven-page biosynthetic discussion), 2) Physico-chemical data (brief tabulations of the principal spectroscopic hand values, oetant rule, and mass spectral fragmentation types), 3) Mona and sesquiterpenes, 4) Diterpenes, 5 ) Sester-, hi-, and higher terpenoids, and 6 ) Steroids.
comments are included where necessary. In the biosynthetic sections, isotopic labels are clearly carried through from precursor to final product. This book is to he particularly eommended for eliminating the need for extensive page-turning by means of the following 1) Trivial names are given directly on the formulas. 2) References are given almost always on the page cited. 3) Structural farmulas are used liberally. Use of R1-, R2-, ete. has been avoided. 4) Graphical representation of nmr data.
The selection of topics gives a good broad general coverage of compound types in the stmctural/synthetic sections, but it is perhaps unfortunate that more biasynthetie work is not covered, since the diagrammatic approach is particularly helpChapters 3-6 are arranged by compound. ful in tracing stereo-specifically labelled The format of the S t N ~ t ~ r d ' S e c t i o n s mevalonate through the metabolic pathways. consists of: 1) Structural formula with seLiterature coverage is chiefly 1965-13 lected spectral data. (When nmr $ empha(not 1972-73 as stated in the foreward). sized, the 6 values are represented directly The format is much like lecture slides or on the structural formula, together with a notes, and should make this book especiallimited number of multiplicities and couly useful to comment just prior to referral olines.) . .. 2) Brief statements of kev,mints of to the original literature. structural analpis (usuall" h i r e d to three In spite of inherent lack of breadth and or four). 3, Partial d ~ ~ r a d a t i obrn converdepth in a work of this nature, it represents sion scheme a timely approach to literature survey and may be recommended, without serious resSynthetic sections consist mainly of diervation, particularly to the non-specialist. agrams with sufficient steps and formulas to enable the reader to grasp the operations James L. Blaarner readily. Reagents are clearly indicated. Temple University Very few yields are given. Supplementary Phiiadeiphia. Pennsylvania 19122
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Creatlon and Detection of the ExcMed State. Volume 3 Edited by William R. Wore, University of Western Ontario, Canada. Marcel Dekker, New York, 1974. viii 193 pp. Figs. and tables. 16 X 23.5 cm. $23.50.
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The detection of photophysid and photochemical mocesses in =cited state* nf ~ ~ molecules presents investigaturs with chal. I~nginaexperimenul problems. The search fur solutions 11, thew problems has prompted the development of an impres. slve array uf sophisticated and highly ype. rialized techniweu and instruments. There is a need far dktailed information on such techniques and instrumentation which is not generally provided in the standard journals. In response to this need, a series of articles which describe methods for establishing specialized experimental tachniques within a laboratory have heen compiled and edited into a multivolume collection entitled "Creation and Detection of the Excited State." Volume three of the series is divided into three chapters which deal with quantitative measurements of chemiluminescence in condensed phases, single vibronic level fluorescence, and the measurement of photoinduced current in solution. In general, each chaoter is directed toward descrihine and illusiratina the advantages and disacc Vnntngea of zpecific experimental tech. nques. The urganuation of each chapter proceeds along similar lines, presentin): a well documented but brief introduction to basic theoretical principles, details of experimental techniques, calibration procedures, experimental artifacts, and reasonably current references to specific vendors and materials sources. Figures and tables for critical pieces of apparatus are clear, well defined, and labelled with the appropriate legend or explanation. Both the hihliography (containing significant references up to 1973) and the table of contents accompanying each chapter satisfactorily document and describe the chapter eontents. However, little or no attention is given , the serious problems of preparative techniques (e.g., purification of solvents, setting up vacuum lines). Obtaining samples of sufficient purity, particularly far photachemical measurements in condensed phawu, ir n nontr:vinl tnsk. Prerumahly, hwuewr, rhis material has hwn ewerrd in earlier chapters of the swiss and discussed in bibliographical references. In the chapter on chemiluminescence techniques, the problems of chemical kinetics, sensitization methods, and radiometry are descrihed in some detail. Cansiderable attention is spent in detailed evaluations and comparisons of several different experimental approaches toward luminescence measurements of photochemical reactions. Features of special interest in this chapter include a list of basic definitions and symbols comma" to the field, and a list of instrument and calibration services. The chapter on single vibronie level (SVL) fluorescence describes the special techniques and conditions necessary for the measurement of the extremely weak fluorescence from low pressure gas samples. SVL experimental conditions and ~
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