Procedure The potential spaces are determined after occupation of selected point con- figurations [I61 in the appropriate space groups with (+)- and (-)-charges using the Ewald procedure applied to prescribed 3D meshes. The PEPS for CsCl is obtained for the charge distribution ( + ) on the Wyckoff positions la and ( - ) o n Ib in PmJm, respectively. Both positions f i x primitive point con- figurations P. That is the pertinent POPS is characterized by A P f E A and is given the symbol P” (ImTm). In the same way the Schwarz D surface is obtained from the combination D::,; A Dii,,; in F&m. Other than hitherto reported!” it belongs to the Cheshire group P n h , since the generating point configurations already have FdJm symmetry. Color pictures: Using DI-3000 graphic software, own programs, and an AED-767 co~orgrdphic screen.

Received: November7, 1985 [ Z 1524 IE] German version: Angew. Chem. 98 (1986) I 1 I

[ I ] R. Nesper, H. G. yon Schnering, 2. Krisrallogr. 170 (1985) 138. [2] R. Nesper, H. G. von Schnering, unveroffentlicht.

BOOK REVIEWS

131 S. Anderson, T. S. Hyde, H. G. von Schnering, Z . KrisraNugr. 168

[4] S. T. Hyde, S. Anderson, Z . KristaNogr. 168 (1984) 221. 151 S. T. Hyde, S . Anderson, 2. Kristdogr. 170 (1985) 225. 161 A. H. Schoen, NASA Technical Nore D-5541 (1970). [7] K . Weierstrass: Marhemotirche Werke 1, Bd. 3. Mayer & Muller, Berlin

181 H. J. Wagner, Computiny 19 (1977) 35. 191 W. Fischer, 2. KrisroNogr. 133 (1971) 18; ihid. 138 (1983) 129: ibid. 140

(1984) I .

1903.

(1984) 50. [lo] W. Fischer, E. Koch, Arra CrystaNoyr. A 32 (1976) 225. [ I I ] A. L. Mackay, Physica B + C (Amsterdam) 131 (1985) 300. [ 121 R. J. Cava, F. Reidinger, B. J. Wunsch, Solid Srore Commun. 24 (1977)

[I31 R. Bachmann, H. Schulz, Solid State lonics Y (1983) 521. [I41 W. Abriel, Acta CrvytaNogr. C39 (1983) 956. [ 151 L Llanos, Dissertarion, Universitst Stuttgart 1982. 1161 T. Hahn (Ed.): International Tables for Crysta1lograph.y. Vol. A , Reidel,

41 I .

Dordrecht, Holland 1983, p. 819ff.

Kristallstruktur und chemische Bindung. By A. Weiss and H . Witte. Verlag Chemie, Weinheim 1983, xi, 396 pp., bound, DM 98.00.--ISBN 3-527-25612-1 In the typical classical German tradition of dividing

chemistry into basic fields, this monograph treats that part of the “physical chemistry of solids” (i.e. with a minimum of compounds) which is concerned with the relationships between physical properties, structures, and chemical bonding. This vitally necessary and until now missing con- tribution is intended for students in the second half of their courses, but is also quite suitable for experienced col- leagues in university and industry who require basic infor- mation concerning this area of chemistry. It would be de- sirable for this book, which is written by leading experts in the field, to become a part of the miniaturized “library” of young chemists, since basic knowledge of this particular field is going to be necessary in the future. The treatment is deliberately kept simple and the most important areas are discussed in about 200 pages divided into seven sections, namely: lattice energy and its importance for the stability of solids; the band model for metals and semiconductors; the importance of the typical cooperative properties for solids and their connection with structure and bonding; the importance of anisotropy in solids; lattice dynamics; defects in solids; high polymers and amorphous materials. These are preceded by two chapters on the fundamentals of crystallography and chemical bonding. An important section amounting to 90 pages then follows describing ex- perimental methods such as diffraction, angular momen- tum methods, Mossbauer spectroscopy, optical methods, X-ray and photoelectron spectroscopy, and Compton scat- tering. Essential data and relationships are included in an appendix, as well as a structural discussion using the min- eral olivine as an example.

As terse an introduction as that in this monograph is un- likely to escape the wishes of colleagues of the main field for supplementation and change. A few of these are: ( I ) the difference between lattice and structure must be de- fined and employed without compromise; (2) the funda- mental importance of symmetry, not just for crystalline materials, is not nearly enough emphasized; (3) specific heats, magnetism, magnetic fields, conductivity, low tem-

peratures, high pressures d o not find a place under the im- portant experimental methods; (4) with respect to the topic of this book, the selection of substances is very limited and the choice of structures conveys a dangerous impression to the reader that only a dozen examples are required for an understanding of the relevant relationships. This book has been well produced by the publisher, but was it really nec- essary that each fraction, each root sign etc. should inevita- bly lead to a doubling of the line spacing?

[NB 681 IE] Max-Planck-Institut fur Festkorper-

forschung Stuttgart (FRG)

Huns-Georg von Schnering

1,3-Dipolar Cycloaddition Chemistry. Edited by A . Pudwa. Wiley Interscience, New York 1984. Volume I : xiii, 817 pp.; Volume 11: xiii, 704 pp., hardback, together $392, ($ 292 in USA).-ISBN 0-471-00354-X 1,3-Dipolar cycloadditions were first carried out by

Buchner in 1888 with esters of diazoacetic acid. Many other examples followed; however, the fundamental prin- ciple of this reaction was not recognized until the pioneer- ing formulation of the general concept by Huisgen, also at Munich. 1,3-dipolar additions play an important r6le in the synthesis of heterocycles and also, increasingly, in the regio- and stereoselective construction of carbo- and acy- clic compounds. The great advances with regard to the the- ory and mechanism of these reactions are due to the work of the Munich school, the formulation of the Woodward- Hoffmann rules, and the application of Fukui’s frontier or- bital concept, in particular by Sustrnunn, Bastide, and Houk. The reactivity and the regioselectivity of the con- certed-asynchronous 1,3-dipolar cycloadditions can thus be satisfactorily interpreted or predicted in many cases. Yet, until now a comprehensive account of this area was not available, in spite of many monographs or chapters dealing with separate aspects (this is equally true for the even more famous sister reaction, the Diels-Alder addi- tion).

A. Pudwa, together with a further 18 authors from six countries, has now succeeded in producing a collective

1 12 0 VCH V~~rluysge~e/ / .~cl iqfr mhH. 0-6940 Wernhrim. 1986 0570-0833/86/0101~01 12 S 02 S(J/O Angew. Chem. In/. Ed. Engl. 25 11986) NU I

volume of ca. 1500 pages that will fi l l this gap for many years, albeit in a not entirely satisfying way.

R . Huisgen’s introductory chapter (Introduction, Survey, Mechanism. 176 pp. with 522 references) consists of a highly readable excursion through the history of this chemistry. It covers all aspects of 1,3-dipole reactions, pre- sented concisely, clearly and with exemplary formula sche- mes. Although stress is laid on the essential Munich contri- butions, the (self)critical commentaries on the entire ar- senal of methods available for mechanistic studies are a delight, with terse general introductions in each case, pointing out the relationships to other reaction types, with practical directions and topical observations. This is infor- mative reading for anyone interested in reaction mecha- nisms in particular, or in the formulation, development, and consolidation of one of the great general concepts of organic chemistry!

The subsequent chapters are concerned with the most important classes of 1,3-dipoles, above all those involving C, N and 0 [chapters 2-1 1 ; oxyallyl is dealt with, carbonyl ylides are not (?)I as well as with the unifying principles (chapters 12-15). In detail: nitrile ylides (2; Hansen, Heim- gartner. 114 paged231 references); nitrile oxides and im- ines (3; Caramella, Griinanger, 102/552), diazoalkanes (4; Regztz. Hrydt. 166/714); azides and N 2 0 (5; Lwowski, 941 253), azomethine ylides (6; Lown, 80/182); azomethine im- ines (7; Grashey. 84/394), mesoionic ring systems (8; Ports, 82/203); nitrones (9; Tufariello, 86/384); azimines, azoxy and nitro compounds (10, Storr, 32/65); ozone and carbo- nyl oxides ( I 1 ; Kuczkowski, 80/194); intramolecular 1,3- dipolar cycloadditions (12; Padwa, 130/388); theory of 1,3-dipolar cycloadditions (13; Houk, Yamaguchz, 44/89); 1,3-dipolar cycloreversions (14; Bianchi, Gandolfi, 921 4 19); higher order dipolar cycloadditions (1 5 ; Crabb, Storr, 52/98). Both volumes are carefully edited; printing mis- takes and errors of fact are rare in the text and in the nu- merous formula diagrams, as well as in the author and sub- ject indices (65 and 40 pages, respectively).

Each author is known for his research in the area he deals with, and together they present competent and, for the greater part, systematic surveys organized according to their own interests. I should like to single out chapters I , 2, 4, 7, 9, 12 and 14 as being “reader friendly” (systematic arrangement; up-dated literature coverage; experimental details/yields; interesting cross-references and sugges- tions). It should be noted that the entire project has, in my opinion, been concluded rather carelessly. Points at issue: “coordination of the chapters”, “formula diagrams”, “cut- off date/up-dating of literature references”, “current de- velopments and outlook”, “price”. As is often the case with multi-author projects (cf. the Patai series), the individ- ual chapters are not coordinated. Thus, for example, about half of the contents of chapters 12 and 15 can be found elsewhere. Chapter 11 presents an extensive discussion of the individual steps of alkene ozonolysis and on117 this (80 pages, with one reference from 1982); later a more precise and up to date synopsis appears (chapter 14, 8 pp., 20 ref- erences from 198213). Discussions on mechanisms, reactiv- ity, and regioselectivity occur in many sections on the indi- vidual dipoles, although these subjects comprise the gen- eral theme of chapters 1 and 13!

Two of the 15 chapters contain clearly laid out formula schemes, probably executed by the authors. The rest seems to have been produced by the press: sprawling, badly set out, with bond angles and spatial formulas that are out of question (by contrast, those of the ApSimon series of the same press are excellent).

The cut-off date of the literature references, very impor- tant to the user, is dealt with pitifully. The foreword dates from March 1984; no indications appear in the individual chapters, which were obviously concluded in 1980/1 (a praiseworthy exception is chapter 7). Gratefully, a few au- thors (chapters 2, 4, 7, 9, 12, 14) make use of addenda to bring their contributions up to date, i.e. to the end of 19821 1983, as can be learnt by examining the lists of references. Thus, recent developments in this field are sometimes not covered (cf. Nuchr. Chern. Tech. Lab. 32 (1984) Vol. 10 and 11): a) the Vedejs method (1979) for the generation of syn- thetically useful 1,3-dipoles without aryl substituents; b) stereoelectronic effects in the use of chiral dipoles or dipo- larophiles.

The present volumes appear at the end of a long era in which, thanks to Huisgen, these reactions have developed from being mechanistically puzzling curiosities to being theoretically attractive and rationalizable ones, and fur- ther, have advanced to the point of being useful, because of being “predictable” tools in organic synthesis. Adding 3 + 2 the right way is going to become routine (it is in part already) and will have fruitful repercussions on the recog- nition and solution of new theoretical problems. These sur- veys will play their part in that.

Summary: A few deficiencies notwithstanding, the Padwa books are a rich mine of information for any chem- ist involved in reaction mechanisms, cycloadditions, heter- ocycles or stereoselective synthesis. For the newcomer they offer a stimulating starting point. Without doubt, this en- terprise will be a commercially successful one; however, the horrific cost of these volumes will probably make them library-shelf copies only, against the intention and to the alarm of many of the authors involved.

Volker Juger [ N B 6861 Institut fur Organische Chemie

der Universitat Wurzburg (FRG)

Total Synthesis of Natural Products: The “Chiron” Ap- proach. By S. Hanessian. Pergamon Press, Oxford 1983. xvii, 291 pp., Paperback, L 11.25.--ISBN 0-08-0307 15-9 The utilization of carbohydrates as chiral building

blocks for the synthesis of enantiomerically pure target molecules has, in recent times, become one of the most powerful and versatile synthetic strategies. Due to some unique advantages, such as low cost, flexibility and effi- ciency, this approach has been used extensively for the synthesis of complex natural products. The vast amount of synthetic work done in this area, in conjunction with the high potential for widespread applications, dictated the need for an authoritative monograph on the subject. Stephen Hanessian, who has been a long time leader in the conceptual development and exploitation of this technolo- gy, was able to produce an excellent “how-to” monograph, filled with a plethora of well-analyzed examples.

The book is divided into sixteen chapters, arranged in seven parts (Basic concepts, Design, Discovery and Execu- tion). Chapters 1-4 give a general introduction to the sub- ject and illustrate the basis of this methodology, by giving some guidelines on how to analyze a target molecule in terms of carbohydrate-derived precursors. The author sug- gests here the use of the term “chiron” to describe these enantiomerically pure synthons. Chapters 5- 10 deal with the synthesis of natural products with “apparent carbohy- drate-type symmetry”, such as those having a tetrahydro- furan or a tetrahydropyran ring. Justifiably, this section of

1 I3 Angew Chern I f i t Ed. Engl 25 11986) No. I