OxygenÐA Play Not Just For Chemists?

Oxygen. By Carl Djerassi and RoaldHoffmann. Wiley-VCH, Weinheim2001. viii � 120 pp., PaperbackDM 29.80 (ca. E 15).ÐISBN 3-527-30413-4

This year marks the one-hundredthanniversary of the awarding of NobelPrizes by the Nobel Foundation. Imag-ine that to mark this centennial, thefoundation decidesto award a ªretro-Nobel Prizeº forthose great discov-eries in chemistrythat occurred be-fore the first prizewas given. The taskof making thisaward is the con-text of the playªOxygenº, which had its world premiereon April 2, 2001 at the San DiegoRepertory Theater. This date coincidedwith the opening of the national springmeeting of the American Chemical So-ciety in San Diego on the occasion of its125th anniversary, and the audience waspacked with members of that field.ªOxygenº was written by two world-famous chemists, Carl Djerassi of Stan-ford University and Roald Hoffmann ofCornell University; both have increas-ingly pursued literary work after receiv-ing almost all the accolades possible intheir respective research fields. The playconcentrates on finding the first retro-Nobel in chemistry.

Of course, many choices are possiblefor this great honor. One candidate that

springs to my mind is Amedeo Avogadro(1776 ± 1856), who in 1811 put forwardthe hypothesis that equal volumes of gasat the same temperature and pressurecontain equal numbers of atoms ormolecules. Indeed, Avogadro firstcoined the word ªmoleculeº and intro-duced the concept that substances couldbe polyatomic. Another most worthycandidate is Jöns Jacob Berzelius(1779 ± 1848), noted for his determina-tion of atomic weights, the developmentof modern chemical symbols, his electro-chemical theory, the discovery and iso-lation of several elements, the develop-ment of classical analytical techniques,and his investigations of isomerism andcatalysis (both named by him). But thenyou would not have a play! Instead, theretro-Nobel committee struggles withmaking the award for the discovery ofoxygen. There are three contenders. Thefirst is Carl Wilhelm Scheele (1742 ±1786), the Swedish apothecary who isthe first to discover ªfire-airº but fails topublish this discovery until 1777. Thesecond is Joseph Priestley (1733 ± 1804),the English Unitarian minister who dis-covers oxygen but clings dogmatically tothe theory of phlogiston, which says thatall flammable materials contain an odor-less, colorless, weightless substance(phlogiston) that escapes upon burning.Hence, Priestley fails to understand thetrue significance of what he has found.The third candidate is the French chem-ist and tax collector Antoine Laurent deLavoisier (1743 ± 1794), who was the firstto recognize that combustion involvedoxidation. By denying the existence ofphlogiston, Lavoisier was able to estab-lish the principle of conservation of massin chemical reactions.

The play skillfully jumps back andforth between the time periods of the1770s and the present as the Nobel Prizecommittee grapples with this choice. Atfirst, the task seems to be an easy one,with Lavoisier the first choice as thefather of modern chemistry. But the plot

thickens when it is revealed that he hadthe benefit of much knowledge of thework of his competitors. In 1774 Priest-ley, a guest in Lavoisier�s home in Paris,told him how he had made what hecalled dephlogisticated air. At approxi-mately the same time, Scheele wroteLavoisier a letter detailing his discoveryof fire-air and how to make it. BothPriestley and Scheele believed in phlo-giston, but Lavoisier was able to com-prehend the true significance of oxygenin combustion. As they say, the rest ishistoryÐbut do we really know the truestory? Djerassi and Hoffmann captureand amplify the moral dilemma ofwhether Lavoisier gave sufficient creditto those whose work he used to over-throw the theory of phlogiston.

Ask someone what ºoxygenº means.To scientists the answer is obvious, andthe only clarification needed is an an-swer to the question, Atomic or molec-ular? But to many, oxygen has othermeanings than simply the life-givingstuff of air. If you doubt this, check thisaddress: http://www.oxygen.com/. Youwill find a Web site devoted to awoman�s view of the world. This siteconnects you to what is one of the mostaudacious entertainment start-ups indecades. Oxygen is the first online andon-air network for women by women; itis now on cable TV in the United States.Its slogan is ªAnother Great Reason toBe a Woman,º and its special spokes-person and salesperson is Oprah Win-frey, perhaps the world�s best known,most influential, and richest TV person-ality. Djerassi and Hoffmann�s ªOxy-genº plays on this association of theword. Throughout their play, what wom-en have to say takes on more significancethan what is said by men.

The chair of the retro-Nobel PrizeCommittee is Astrid Rosenqvist, an out-standing theoretical chemist who hadsome past romantic involvement withanother committee member, Bengt Hjal-marsson. A lovers� quarrel runs through-

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This section contains book reviews and a list ofnew books received by the editor. Book reviewsare written by invitation from the editor. Sug-gestions for books to be reviewed and for bookreviewers are welcome. Publishers should sendbrochures or (better) books to the RedaktionAngewandte Chemie, Postfach 10 1161, 69451Weinheim, Germany. The editor reserves theright of selecting which books will be reviewed.Uninvited books not chosen for reviews will notbe returned.

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out the dialogue. Two other distinguish-ed men complete the committee. Rosen-qvist introduces Ulla Zorn, who is sup-posed to be present only to record themeeting. But Zorn is more than anamanuensis; it unfolds that she is pursu-ing a doctorate on the role of women inthe history of science. As the wranglingover the candidates for the prize inten-sifies, her role changes, and she tells themen that to select properly among thethree contenders it is necessary to askthe women most closely associated withthem. We are treated to a steamy scenein a sauna that involves the fictionalencounter of the prim 35-year-old MaryPriestley, wife of Joseph Priestley; the26-year-old Sara Margaretha Pohl,Scheele�s devoted housekeeper whomhe would marry on his deathbed; and theworldly 19-year-old Marie-Anne Pier-rette Pauize Lavoisier, whom Lavoisiermarried when she was 13. The playargues that these three women weremuch more than bystanders to the sci-entific accomplishments of their malepartners. For example, did MadameLavoisier intercept Scheele�s letter toher husband and keep it secret fromhim? In view of the many complicationsconcerning the discovery of oxygen,what was the final choice of the retro-Nobel committee? Djerassi and Hoff-mann resolve the conflict brilliantly, butI will not give away the ending.

Having served on and chaired severalprize committees, I felt that the carpingremarks of the members of the retro-Nobel committee resembled more afaculty appointment process gone terri-bly awry than the serious deliberationsof a prize selection. I asked Sture ForseÂnof Lund University, a member of theChemistry Nobel Prize Committee for19 years, what his impressions were. Heagreed with me that the play shows morea caricature than a picture of whattranspires in such deliberations. Ofcourse, playwrights are allowed to takeliberties, and ªOxygenº does just that. Itprovides a most diverting and entertain-ing evening for chemists and those whoponder the nature of discovery and theattribution of discovery to individuals.

Djerassi is well known for his work inthe synthesis of steroid oral contracep-tives and for the development of mass-spectrometric techniques. He wrotemore than 1,200 articles in the area of

chemistry before turning to what he callsªscience in fiction.º He is the author ofseveral novels, including ªCantor�s Di-lemmaº, ªThe Bourbaki Gambitº,ªNOº, ªMarx, Deceasedº, and ªMenac-hem�s Seedº, as well as a play based onthat novel, ªAn Immaculate Misconcep-tionº. He has also written his memoirsand two autobiographies, ªSteroidsMade It Possibleº (for chemists) andªThe Pill, Pygmy Chimps & Degas�Horseº (for nonscientists). Awards andhonors received by Djerassi include theNational Medal of Science in 1973, andthe American Chemical Society�s high-est honor, the Priestley Medal, in 1992.

Hoffmann won the 1981 Nobel Prizein chemistry for theories concerning thecourse of chemical reactions. He sharedthe prize with the late Kenichi Fukui.Hoffmann�s literary works include booksof poems, ªThe Metamict Stateº (1987)and ªGaps and Vergesº (1990); ªChem-istry Imaginedº (1993), a book about art,science, and literature written with theartist Vivian Torrence; ªThe Same andNot the Sameº (1995), an account of thedualities in chemistry; and ªOld Wine,New Flasks: Reflections on Science andJewish Traditionº (1997), a book hecoauthored in an intertwining of voicesof science and religion. He is also arecipient of the National Medal ofScience (1983) and the Priestley Medal(1990).

Science in theater is emerging as anexciting new art form. It can be seen insuch plays as Tom Stoppard�s Arcadia,which revolves around a 13-year-oldmath prodigy, Thomasina Coverly, whobaffles her tutor by asking if God is aNewtonian, and Michael Frayn�s Copen-hagen, which is based on the uncertain-ties surrounding the 1941 meeting be-tween the physicists Niels Bohr andWerner Heisenberg in German-occu-pied Copenhagen.

We are indebted to Carl Djerassi andRoald Hoffmann for showing the worldthat chemistry can also be theater. Thepremiere audience, almost a Who�s Whoin chemistry, was greatly amused by theplay; it remains to be seen whether it willalso appeal to a less knowledgeableaudience.

Richard N. ZareDepartment of Chemistry

Stanford University, Stanford, CA(USA)

Chemical Synthesis of NaturalProducts. Edited by Karl J. Hale.Sheffield Academic Press, Sheffield2000. xiii�429 pp., hardcover£ 99.00.ÐISBN 1-84127-039-3

Natural products have long played animportant role in organic chemistry. Onone hand they present challenges forchemists involved in determining theirstructures, while on the other handsynthetic chemists devote their effortsto the rewarding and satisfying task ofconstructing these fascinating structures,which are often associated with usefulbiological effects, by the most elegantroute. This latter area of endeavor is thesubject of this book, in which Karl J.Hale, assisted by 19 co-authors, sets outto report on developments in recentyears. The work is intended for estab-lished researchers in industry and uni-versities with interests in the synthesis ofnatural products. Everyone within thisintended readership is likely to findsomething useful in the book�s 12 chap-ters, although it is not possible for it tocover the subject exhaustively in a littleover 400 pages, nor does it claim to do so.

In Chapter 1 (39 pp.) J. M. Gardinerdescribes strategies for the synthesis ofcomplex carbohydrates, including bothchemical glycosylation methods and en-zymatic methods. Developments in thearea of solid-phase syntheses of oligo-saccharides and oligosaccharide librariesare also described, and the chapter endswith syntheses of oligosaccharide ana-logues and glycomimetics. In Chapter 2(23 pp.) J. W. Bode and E. M. Carrieradiscuss the synthesis of some macrolides,namely oleandolide, fluvirucin B1, mac-rolactin A, and lankacidin. For each ofthese, several methods of synthesis areoutlined, and important key steps arediscussed in detail.

Chapter 3, by A. N. Hulme (33 pp.), isconcerned with the total synthesis ofpolyether antibiotics. After briefly sur-veying the most important compoundsand their properties, the author discussesbiomimetic syntheses of polyether anti-biotics in greater detail. Next, as in theprevious chapter, syntheses of someindividual compounds of this class aredescribed, namely salinomycin, spongi-statine, parviflorin, asimicin, and breve-toxin A, the last of these being onlybriefly outlined in three pages.

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In Chapter 4 (30 pp.) J. Robertsonreports on important developments inthe total synthesis of alkaloids. Synthesesof reserpin, daphniphyllum alkaloids,dendrobin, gelsemin, strychnine, mor-phine, roseophyllin, and many othersare described.

Chapter 5 (16 pp.), by G. A. Sulikow-ski and M. M. Sulikowski, is devoted tothe synthesis of heteroaromatic naturalproducts, including durocarmycin A,mitomycin K, and camptothecin. InChapter 6 (36 pp.) R. S. Coleman andM. L. Madras are concerned with aro-matic natural products, including no lessthan 87 (!) compounds. Some of thesereceive no more than a mention, butothers chosen as representative of typesof compounds are treated in thoroughdetail. Some worth noting are michell-amines, dibenzocyclooctadiene-lignans,podophyllotoxins, quinones such as con-ocurvone or dynemicin A, and chro-manes such as calanolid A, calanolid B,and angucyclins, to mention only a few.

In Chapter 7 (18 pp.) E. Tyrell gives ashort survey of developments in the areaof terpene syntheses, but includes only afew sesquiterpenes (e.g., seychelles,longifoles, a-cedrene, quadrone, and tri-quinanes) and some diterpenes (clero-dans, labdans, vinigrol, kaurane, etc.).

Chapter 8 (30 pp., C. M. Marson)describes new developments in the syn-thesis and modification of steroids, be-ginning with reactions involving thesteroid skeleton, followed by approachesto total and partial syntheses. Polyenecyclizations, electrocyclic reactions, andfree radical cyclizations are described,and the chapter ends with syntheses ofheterocyclic steroids, in particular ceph-alostatins. In Chapter 9 (35 pp.) S.Caddick, S. Shanmugathasan, and N. J.Smith discuss syntheses of enediynes anddienediynes. Research projects on syn-theses of calicheammicines, esperami-cines, dynemicines, and neocarcinostatinchromophores, including model studies,are described in detail.

Chapter 10 (36 pp., C. M. Bladon andP. B. Wyatt) is concerned with the syn-thesis of amino acids and linear peptides.Various strategies for solid-phase syn-thesis are described, including the use ofresins, linkers, and coupling reagents,and methods based on fragment con-densations and chemoselective couplingby Kent�s method. This is followed by a

brief excursion into combinatorial pep-tide chemistry, and finally a very detaileddescription of methods for the stereo-selective synthesis of a-, b-, and g-aminoacids.

In Chapter 11 (36 pp.) A. B. Taborreviews recent developments in the syn-thesis of cyclic peptides, then focuses onindividual examples of these com-pounds, giving most space (10 pp.) tovancomycin. In the final chapter (57 pp.)K. J. Hale, G. S. Bhatia, and M. Frigeriopresent a survey of work on syntheses ofcyclodepsipeptides. Those on which theyreport include arenastatin A, dolastatinD, himastatin, sanglifehrin A, and di-demnin A, to name only a few.

Most of the reaction schemes give allsteps of the synthesis in a concise form.However, a few of them concentrateonly on one or two key steps, indicatingthe others merely by a sequence ofarrows labeled as ªstepsº (an unsatisfac-tory practice in my view). Scheme 2.28fails to include the reaction conditionsand the reagents, and Scheme 7.24 ap-pears to have been produced with differ-ent parameter settings of the graphicsprogram, as becomes immediately obvi-ous on turning the pages. Otherwise theeditorial work has been done with greatcare (with one exception mentionedbelow), so that one finds very fewprinting errors. However, a glossary ofabbreviations would have been a usefulimprovement. The legends to the reac-tion schemes contain many abbrevia-tions which are seldom explained in thetext. Often the index offers no help withthese, for example in Scheme 1.1 withthe abbreviation DTBMP. It is only byaccident that one discovers, from thelegend to Scheme 1.2, that this mustmean di-tert-butyl-4-methylpyridine.There are many similar examples inevery chapter.

However, these criticisms do not de-tract significantly from the good overallimpression. Altogether the book offers agreat wealth of information for thoseworking in the field. Nonspecialists toowill benefit from the excellent overviewsof compounds with interesting structuresand important biological and/or phar-maceutical activity, and of synthesesachieved during the past ten years. Thechapters cover the literature up to 1998,and wherever possible they refer thereader to up-to-date review articles,

especially on aspects that had to beomitted or only touched on briefly inthe book. Everyone active in this area ofresearch in industry or academia willcertainly find new and stimulating ideasin at least one or other of the chapters,and from the literature references pro-vided (over 1500 in the book as a whole)should be able to go directly to thelibrary to read the relevant originalpublications. Those involved in teachingwill likewise find the book useful andstimulating, and will be able to incorpo-rate some of the syntheses into theirlectures and laboratory exercises.

Johann JauchInstitut für Organische Chemie

und BiochemieTechnische Universität München

Munich (Germany)

Ligand Field Theory and its Appli-cations. By Brian N. Figgis andMichael A. Hitchman. Wiley-VCH,New York 2000. xviii�354 pp.,hardcover £ 51.95.ÐISBN 0-471-31776-4

This book is the first of a plannedseries of one-volume introductions toimportant areas of inorganic chemistry.Compared with its predecessor of 1966,Introduction to Ligand Fields by BrianN. Figgis, two chapters have been re-moved and replaced by new ones. Theauthors have removed the chapters ongroup theory and molecular orbitaltheory, assuming that readers are al-ready familiar with these topics, andhave introduced chapters on the angularoverlap model and on the origin andcalculation of splitting of the d-electronenergy levels in cubic ligand fields. Thecontents of all the other chapters areunchanged in principle, but they havebeen updated, rearranged to some ex-tent, and given new titles.

The book is divided into eleven chap-ters. The first four are concerned with acommon theme, which can be defined asthe description of the ligand field effecton the basis of models. Chapter 1 isdevoted to the ligand field concept andits application to the interpretation ofthe physical properties of complexes(stability, structure, spectroscopy, mag-

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netic properties). Chapter 2 gives adetailed description of the parametriza-tion scheme based on the point chargemodel, as applied to d ions with octahe-dral and tetrahedral coordination, in-cluding variants with tetragonal andtrigonal distortion. Other parametriza-tion schemes for d- and f-electron sys-tems are mentioned, and the limitationsof the electrostatic model are discussed.Chapter 3 introduces the angular over-lap model (AOM) and discusses itsspecial characteristics. Energy expres-sions for common types of complexsymmetries are derived. Examples oftypical AOM parameter values are giv-en, the advantages of the model com-pared with the electrostatic approach areexplained, and attention is drawn tosome computer programs for calculatingspectroscopic and magnetic properties.Chapter 4, on the origin and calculationof splitting of the d-electron energylevels in cubic ligand fields, presentsresults from point charge and molecularorbital calculations of the ligand fieldsplitting and compares them with exper-imental data.

The next two chapters form a secondtheme: perturbations of d electrons.Chapters 5 and 6 briefly discuss someimportant aspects of the theory of freeions and that for ions in complexes(perturbation of the d-electron systemby interelectronic interactions, spin ±orbit coupling, and ligands). Perturba-tions of the latter type are subdividedinto effects of weak, intermediate, andstrong ligand fields, and are discussed onthe basis of correlation diagrams andTanabe ± Sugano diagrams.

The third subject group, Chapters 7 ±9, is concerned with the physical proper-ties of complexes, beginning with theinfluence of the d-electron configurationon structure and stability (Jahn ± Tellereffect, bond lengths, enthalpy of hydra-tion, kinetics). Chapter 8 then moves onto electronic spectra (intensities, selec-tion rules, band broadening, tempera-ture effects), with typical examples fromthe 3d, 4d, and 5d element series (in-cluding the spectrochemical and neph-elauxetic series, charge transfer, andluminescence). Lastly, Chapter 9 dealswith the magnetic properties of free andcomplex-bound ions, the latter beingclassified according to the ground-stateterm (A, E, or T) in a cubic ligand field.

The topic is completed by brief discus-sions of spin-crossover compounds andpolynuclear exchange-coupled com-pounds.

Chapters 10 and 11 are concerned withthe EPR spectra of complexes (charac-teristics of the spectra, spin operators,interpretation of EPR parameters) andwith actinide compounds (ligand fieldeffect in f-electron systems, UV/Visspectra, magnetic properties). Finallythere is an appendix with sections listingspherical harmonics, matrix elements,alternative ligand field parameters, en-ergy terms, orbital angular momentumoperators, and other data.

One of the favorable impressionsgained from reading this book resultsfrom the authors� treatment of thevarious aspects of ligand field theoryunder well defined and self-containedsubject areas. Chapters 7, 8, and 10,perhaps the most important in the book,succeed well in their concise, systematic,and informative description of the phys-ical properties, including 1) the influenceof the d-electron configuration on struc-ture, stability, and kinetics, 2) the inten-sity, width, and shape of absorptionbands, including temperature effects,and 3) EPR spectra. Here readers areprovided with important and usefulcriteria for interpreting their own re-search results.

Nevertheless, the overall impressionsare mixed. It is essential for the reader togain a clear understanding of many otherareas of theory treated in the text (suchas angular momentum operators), butthat is hindered to some extent bymisprints in important formulas, a lackof mathematical strictness, and poortypography in some of the mathematicalequations. In transfering passages fromthe earlier volume, the publishers havenot only carried over some existingprinting errors (e.g., in Equations 1.31,2.62, 5.7, 8.12, 9.12, and 9.14) but haveintroduced some additional ones (e.g., inEquations 7.16, 9.83, and 9.95). Someconfusion results from the use of at leastfour different notations for the angular-and spin-dependent state functions,where it would have been better to usethe Dirac formalism throughout. More-over, for the reader it is almost impos-sible to identify an operator as such, andthe use of bold-type symbols is notsystematic. In equations involving the

magnetic susceptibility (in SI units), themagnetic field constant is missing. Occa-sionally the reader is left without helpwhere symbols are not explained (e.g., inChapter 3, Table 3.1), and appropriateliterature references are not given. Someof the figures are unclear and incomplete(e.g., Figs. 6.11, 6.15, and 9.1). Finally,the authors have omitted some impor-tant results that are essential for an up-to-date monograph on ligand field ef-fects, such as the application of theangular overlap model to lanthanidecompounds, the LIESST effect in spin-crossover compounds, and quantum-me-chanical calculations of exchange pa-rameters for dinuclear copper com-plexes. Although all these are compara-tively minor weaknesses, they areannoying for readers with only a limitedknowledge of the subject. Were it not forthese shortcomings, one could recom-mend this as a well balanced, practical,and readable monograph on an attrac-tive area of inorganic chemistry.

Heiko LuekenInstitut für Anorganische Chemie

Technische Hochschule Aachen(Germany)

Molecular Catenanes, Rotaxanesand Knots. Edited by Jean-PierreSauvage and Christiane Dietrich-Buchecker. Wiley-VCH, Weinheim1999. xiv� 368 pp., 302 figs.,5 tabs., hardcover DM 248.00 (ca.E 127).ÐISBN 3-527-29572-0

This well crafted book on interlockedmolecules is an indispensable guide to avibrant area of modern chemical re-search.

Chapters by Sauvage, Stoddart, andVögtle cover high-yield synthetic ap-proaches to catenanes, rotaxanes, andknots. Raymo and Stoddart review pseu-dorotaxane formation from crown ethersthreaded with alkylammonium mole-cules and the at-tachment of bulkygroups or ªmolec-ular stoppersº tocreate rotaxanes.Multiple bindingsites on threading

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groups are also covered, showing howmolecular switches and shuttles may beconstructed. Macrocycles and threadingmolecules containing paraquat moietiesare also given as examples of rotaxane-and catenane-forming systems utilizingp ± p stacking for self assembly. Use ofamide hydrogen bonding is examined,and a final section on cyclodextrins andtheir application to rotaxane and cate-nane formation completes this chapter.The chapter by Heim, Udelhofen, andVögtle expands on amide-based cate-nanes and rotaxanes touched on byStoddart�s chapter. The relationship be-tween structure and catenane or rotax-ane yield is discussed in depth. Post-interlocking derivatization of catenanesand rotaxanes is discussed and the prop-erties of these new molecular topologiesare reviewed.

Dietrich-Buchecker, Rapenne, andSauvage concentrate on the trefoil knotand the use of copper(i) complexes astemplates for the molecular knottingprocess. The last section of this chapteris quite fascinating, as it describes howthe enantiomerically pure molecular tre-foil knot was prepared. The trefoil knotis topologically chiral, and this sectionshows how the topology fundamentallydictates the physical properties.

Particularly pleasing is the inclusion ofa theoretical chapter on knot theory andchirality by Flapan that tackles thesubject in a concise and simple manner.Judicious use of diagrams makes thischapter much easier to understand thanmany books that cater for the moremathematically minded scientists.

Polymer chemistry makes an appear-ance in three chapters, where polymerentanglements and knotting, polycate-nanes, and polyrotaxane synthesis arecovered in some detail. The chapterªPolymer Chains in Constraining Envi-ronmentsº by J. E. Mark will be ofinterest to those wanting some idea ofwhat physical properties catenane- androtaxane-derived materials might have.Catenane polymers are introduced in achapter by Geerts with the topology ofinterlocked structures that may be in-corporated into polymers. Larger struc-tures formed by the catenation of cyclicpolymers are also discussed. Nomencla-ture, topology, and synthesis of polyro-taxanes are covered in a chapter byGong and Gibson. The chapter is con-

veniently divided according to the dom-inant force that drives the self-assemblyprocess which includes statistical thread-ing, hydrophilic ± hydrophobic interac-tions, hydrogen bonding, metal tem-plates, and p ± p stacking. The finalsection on properties and potential ap-plications will be of interest to supra-molecular chemists and polymer chem-ists alike.

A glimpse of biological aspects ofinterlocked molecules can be seen inªSynthetic DNA Topologyº, by Seeman.

Although this book�s principal attrac-tion is the way it covers a wide range oftopics, perhaps the inclusion of chapterson coordination polymers and molecu-lar-based magnets widens the subjectmatter too far. Having said this, it doesno harm to see how crystal engineeringand materials science are related tointerlocked structures.

In summary the book has clear, welllaid out figures, the chapters do notunduly suffer from repetiton of material,and the index compilation is thorough.The book will be well received, not onlyby those actively researching in this area,but also for people simply curious aboutknotting, threading, or weaving on amolecular scale.

Thomas CliffordDeptartment of Chemistry

University of Kansas, Lawrence, KS(USA)

Oligosaccharides. By Helen Osbornand Tariq Khan. Oxford UniversityPress, Oxford 2000. 112 pp., paper-back £ 16.99.ÐISBN 0-19-850260-5

The selective linking of monosacchar-ides to form complex carbohydrates isone of the mostinteresting areasof natural-prod-ucts synthesis. Al-though the synthe-sis of oligosacchar-ides is still a longway from being aroutine methodcomparable to thesynthesis of peptides or nucleotides,there is still much scope for furtherdevelopment of the techniques. More-over, it enables one to develop protect-

ing groups and strategies for ªtamingºhighly functionalized monosaccharidebuilding blocks, thus making importantcontributions to other areas of organicchemistry research.

This book is an easily readable intro-duction to the present state of knowl-edge on the synthesis of oligosacchar-ides. The authors lead the reader gently,step-by-step, into the complex subject ofcarbohydrate chemistry. Beginning withthe regioselective attachment of protect-ing groups onto the monosaccharidebuilding block, they show how one canproduce protected glycosyl acceptors.There then follows a chapter on donors,in other words on the activation of theanomeric site. Next comes a discussionof the linking of donors and acceptors,and a survey of the latest syntheticstrategies for achieving it. Now onecomes to the real art of oligosaccharidesynthesis, involving the selective remov-al of protecting groups, anomeric activa-tion, and stereoselective bond forma-tion, to which an entire chapter isdevoted. The applications of enzymaticmethods are then reviewed. The bookconcludes with a survey of the capabil-ities and limitations of solid-phase syn-thesis of oligosaccharides.

Altogether this is an excellent bookwhich can be recommended for studentsand practicing chemists who seek anoverview of the current state of thesynthesis of oligosaccharides. In thelimited space of this little book theauthors have, of course, had to omitsome aspects. Thus, there is nothingabout methods for linking more complexaglyca, nor about the far from trivialsubject of the analysis of oligosacchar-ides and their protected precursors. Re-grettably, many of the syntheses de-scribed end at the stage of the fullyprotected oligosaccharide, whereas thefinal deprotecting step presents the mostcrucial challenge in the entire synthesis.

Literature references are given at theend of each chapter, but unfortunatelythese are not in general mentionedexplicitly in the text, which makes itdifficult to go to the original publicationsfor information about exact reactionconditions. It would have been usefulto give detailed information about yieldsand reaction conditions, especiallywhere different synthetic strategies arecompared. Although the figures are

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supported by discussions in the text, it isannoying that, conversely, many of themare not referred to explicitly in the text.

Here, as in other books on carbohy-drates, searching for wrongly drawn ringstructures is both entertaining and in-structive. No less than six different lineformulas are given for N-acetylneura-minic acid, two of which are incorrect.The chapter on the biology of carbohy-drates should be skipped, because un-fortunately it fails to explain the subject.However, apart from these muddledpages, which luckily are very few, thisbook contains an excellent survey of thesynthesis of oligosaccharides, which goesdirectly to the essentials of syntheticmatters without a lot of unnecessarybioorganic embellishment.

Armin GeyerFachbereich Chemie

Universität Konstanz (Germany)

Catalysis and Zeolites. Fundamen-tals and Applications. Edited byJens Weitkamp and Lothar Puppe.Springer-Verlag, Heidelberg 1999.xviii�565 pp., hardcover DM348.00 (ca. E 178).ÐISBN 3-540-63650-1

This book presents in a very clearfashion the fundamental aspects of zeo-lites that account for their extraordinaryproperties as catalysts. The book makesa trip through the areas of synthesis,modification, and characterization ofzeolites, also describing other molecularsieves such as those of the ALPO,SAPO, GAPO, and MEAPO types, andending with the applications of suchmaterials in catalytic processes for oilrefining, petrochemistry, and chemicals.The book will be extremely useful, notonly for newcomers to the field of zeolitecatalysis, but also for researchers anduniversity teachers who will find herethe basic principles needed to under-stand the catalytic behavior of zeolitesand the commercial (and potential)catalytic processes in which they areused.

Readers more interested in zeolitesynthesis will find in the first chapter alucid theoretical treatment of nucleationand crystallization. Unfortunately,

though, the book does not give a morein-depth discussion of the formation ofthe primary nuclei and the techniquesavailable for studying them experimen-tally. I also regretted that I found nodiscussion of the role and design oforganic structure directing agents(SDAs). This limitation is probably dueto the fact that most of the referencesgiven by the authors do not go beyond1991, and consequently all the new SDAsdeveloped for synthesizing SSZ and CITzeolites are not covered. In the secondchapter, on phosphate-based zeolitesand molecular sieves, the fundamentalsare well described, but I expected to findalso a discussion of the catalytic reac-tivity of such materials, especially inview of the fact that they receive verylittle treatment in the following chapters.

The book contains an excellent andinformative Chapter 3 on zeolite mod-ifications, which gives a clear idea aboutthe further gains that can be achieved bypost-synthesis treatments of zeolites.The number of references given by theauthors is outstanding, although it is apity that most of them correspond towork published before 1993. Chapter 4 isalso an excellent chapter that will bevery useful to readers who wish to learnthe techniques available for zeolite char-acterization, with their advantages andlimitations.

The catalytic part of the book hasbeen rationally divided according tozeolites for organic synthesis and thosefor oil refining and petrochemical proc-esses, with special emphasis on shapeselectivity in catalysis. This issue ofzeolite shape selectivity is very welldescribed with up-to-date literature ref-erences. The two chapters on organiccatalysis and zeolites for industrial proc-esses give a very good overview, espe-cially when used in conjunction with thereferences given there.

The book has been carefully edited. Idetected only two citation errors inChapters 1 and 6. The printing is of goodquality and very comfortable to read. Inconclusion, I have enjoyed reading thebook and strongly recommend it tostudents, postdocs, university teachers,and researchers interested in the field ofzeolite catalysis.

Avelino CormaDepartment of Technical Chemistry

University of Valencia (Spain)

Practical Capillary Electrophoresis.2nd Edition. By Robert Weinberger.Academic Press, San Diego 2000.642 pp., hardcover $ 99.95.ÐISBN0-12-742356-7

Capillary electrophoresis has found aplace among instrumental methods ofanalysis, even if not gaining such wide-spread acceptance as the optimistic fore-casts of market analysts led one toexpect. It is a fast microanalytical meth-od, and has become indispensable incertain fields, while in others it is foundin a different guise within analyticalsystems for analyzing proteins andDNA. Several monographs on capillaryelectrophoresis appeared a few yearsago, and now we have a revised andconsiderably enlarged version of a clas-sic work, with 642 pages compared with310 in the first edition. The well-provenstructure of the first edition has mainlybeen retained, although some chaptersand sections have been moved to takeaccount of new developments andchanges of emphasis.

The book is based on lecture courseson capillary electrophoresis which theauthor has given many times. The bene-fits of that are evident in the descriptionsof the various separation techniques, inthe many tables, and in the very instruc-tive figures and examples, together withthe discussions accompanying these. Theintroductory chapters have only beenextended slightly, whereas the mostdrastic, but well justified, changes haveoccurred in the description of the funda-mentals of MEKC (micellar electroki-netic chromatography), and in the use ofcyclodextrins for enantiomer separationin the chapter on ªSecondary Equilibri-um, Micelles, Cyclodextrins, and Relat-ed Reagentsº. The chapter on isotacho-phoresis from the first edition has beenadded instead to the section on ªInjec-tionº, being the only practical applica-tion of this technique as a stackingmethod for preconcentration of tracecomponents. The chapters on ªSize Sep-arations in Capillary Gels and PolymerNetworksº and ªCapillary IsoelectricFocusingº have also been considerablyenlarged, taking into account the prac-tical applications of capillary electro-phoresis in DNA and protein analysis.

In addition to these extensions, theindividual chapters have been improved

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by the inclusion of many new resultsfrom a very wide variety of applicationsof capillary electrophoresis. In many ofthese examples the author also discussespossible sources of error.

To summarize, this second editionreinforces the good impression createdby its predecessor. Because of its highlyinstructive, textbook-style character itcan be recommended for newcomers tocapillary electrophoresis. The experi-enced practitioner may also benefit fromleafing through the book, which shouldyield useful ideas bearing on everydayproblems, and information about possi-ble sources of error and ways of avoidingthem. The comprehensive lists of refer-ences (up to and including 1998) providea good route into the original literature.

Heinz EngelhardtInstrumentelle Analytik, Umweltanalytik

Universität des SaarlandesSaarbrücken (Germany)

Seminars in Organic Synthesis. 25thSummer School ªA. Corbellaº. (Ser-ies: Seminars in Organic Chemistry,Vol. 10.) Edited by Franco Cozzi.Royal Society of Chemistry, London2000. 583 pp., softcover ca. E 50.ÐISBN 99-86208-15-4

This volume is based on the proceed-ings of the 25th A. Corbella SummerSchool, held at Villa Feltrinell, Gargag-no, Italy, on 12 ± 16 June 2000, and is thework of F. Cozzi (seminar chairman)assisted by a team of Italian authors. Thepreface consists of the text of the Gian-carlo Jommi Memorial Lecture, whichwas given by Professor A. Hoveyda(Boston College, USA).

The first main part of the book con-tains the edited texts of the lectures, andis divided into four sections. The firstsection, led by P. Scrimin, containsreports by three authors on some newclasses of compounds with pharmaco-logical activity. These begin with thediscovery and development of a-reduc-tase inhibitors for the treatment ofandrogen-related diseases, followed bya description of the synthesis and ther-apeutic potential of glycine antagonists.The section ends with a report on the

antitumor activity of certain naturalproducts related to taxol.

The second section, under the leader-ship of M. Taddei, discusses new devel-opments in the area of organometallicchemistry, beginning with the use ofcerium(III) chloride as an importantreagent for organic syntheses. This isfollowed by synthetic applications ofchromium carbene complexes.

The third section, led by F. Cozzi,presents reports on new developments inthe area of free-radical chemistry ap-plied to organic synthesis, beginningwith a general discussion of the topic,then focusing on the use of organosele-nium compounds in free-radical reac-tions. Next is a description of someindustrial applications of free-radicalreactions, then the section concludeswith a report of new results in theimportant area of stereoselective free-radical reactions.

The fourth section, led by G. Sodano,is concerned with stereoselective synthe-ses of natural products. The first contri-bution reports on new routes to 2-ami-noalcohols and hydroxylated 2-amino-acids, and their use as intermediates forthe synthesis of nogalamycin analoguesand other compounds. It continues withan account of new methods for thesynthesis of bicyclo[3.2.0]hept-3-en-6-ones and their applications in natural-products syntheses. A second articledescribes the use of epoxides as buildingblocks for the synthesis of natural prod-ucts, and a third reports on total synthe-ses of polyene macrolide antibiotics.

The second main part of the bookcontains reviews of topical themes inorganic chemistry. First T. Benincorireports on applications of organometal-lic compounds in organic chemistry,compiled under a list of topic headings.He begins with a very detailed treatmentof Heck reactions, devoting special at-tention to stereoselectivity in enantiose-lective variants, to domino reactions, andto new catalysts. This is followed by a listof the titles of some papers publishedduring 1999, classified according to themetals. Only the correspondence authoris named for each publication. C. Nativireviews methods for introducing ormodifying functional groups, with com-mentaries on 22 original publications.Topics receiving particular attention in-clude the Baylis ± Hillman reaction, non-

enzymatic kinetic methods for separat-ing racemates of epoxides, the develop-ment of new reaction conditions forimproving long-established reactions,and applications of catalysts other thanorganometallic. A very comprehensivesurvey, classified according to reactiontypes, lists the titles of publications thatappeared in 1999. Next C. De Risi, P.Marchetti, and V. Zanirato contribute auseful review of total syntheses of natu-ral products achieved in 1999. E. Mag-istris presents a review of work publish-ed in the area of solid-phase chemistryduring 1999. As in the preceding chap-ters, some of the publications are dis-cussed in detail, then a more wide-ranging survey of recent work is givenin the form of a list classified accordingto topics.

Considered altogether, this confer-ence report by F. Cozzi and his team ofauthors for the current year provides avery useful survey of new developmentsin organic chemistry during 1999.

Peter LangerInstitut für Organische Chemie

Universität Göttingen (Germany)

Handbook of Molecular Descrip-tors. By Roberto Todeschini andViviana Consonni. WILEY-VCH,Weinheim 2000. xxi � 667 pp.,hardcover DM 498.00 (ca. E 255).ÐISBN 3-527-29913-0

This book is the first to present asystematic survey of the many moleculardescriptors that are used in structure ±activity (QSAR) and structure ± proper-ties correlation analysis. All the manydifferent types of descriptors are includ-ed: physicochemical descriptors describ-ing electronic, lipophilic, and steric sub-stituent effects, the manifold of differenttopological indices, and molecular de-scriptors used in three-dimensionalQSAR analyses. The structure of thebook is on dictionary lines, treatingdescriptors of molecular properties inalphabetical order.

The many cross-references make iteasy to find the relevant entry for aparticular topic, starting from any one ofthe commonly used synonyms; however,some of the cross-references are redun-dant. The strict alphabetical sequence

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has advantages and drawbacks. It makesit easy to find the keyword that one islooking for, but is only of limited help ifone wants to get a quick overview of aset of related descriptors. Fortunately,however, one finds that variants of amolecular descriptor are at least collect-ed together under a common keyword,providing a limited means of obtainingan overview.

The handbook is very comprehensive,and contains practically all the descrip-tors that are used. Also the variationsthat different authors have developedfor individual descriptors are listed. Forexample, under the heading ªelectronicsubstituent constantsº the authors de-scribe 46 types. However, only theoret-ically calculated molecular descriptorsare included; experimental methods andtechniques for generating molecular de-scriptors are not mentioned.

In addition to the above, there arebrief explanations of the basic concepts

underlying the statistical and mathemat-ical procedures used to derive moleculardescriptors. The descriptions of the in-dividual descriptors are complete andthorough, without being too long-wind-ed. The theoretical principles are ex-plained in an understandable way, and insome cases worked numerical examplesare also given to help in understandingthe method of calculation. The treat-ment of each molecular descriptor isaccompanied by references to relevantoriginal literature. The literature refer-ences are very comprehensive, and oc-cupy almost a third of the book.

Values of physicochemical descriptorsare only given for a few substituents, andthere are no tables giving factors that canbe used for calculating descriptors. Toinclude these would make the handbookeven more useful. Unfortunately theauthors also do not direct one to pub-lished tables listing such data, and con-sequently the reader seeking values of

particular descriptors to use in his or herown correlations has to search in theoriginal publications that are cited. Forthe reasons mentioned above, the bookis only of limited value for choosingdescriptors to use in one�s own analyses.Its main value is likely to be for under-standing the descriptors that have beenused by other authors, in cases wherethe exact meaning is unclear to thereader.

In addition to the book�s usefulness asa reference source, one could also bene-fit from simply browsing through it.Through the cross-references the readerwill often discover interesting and pre-viously unnoticed aspects of the molec-ular descriptors treated.

Michael WiesePharmazeutisches Institut

Universität Bonn (Germany)