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-
.
.
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.
.
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
.. .
Type.
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.
-
+
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
-
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.
+
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
