Chemical Education Today
Book & Media Reviews
Heterocyclic Chemistry by Malcolm Sainsbury The Royal Society of Chemistry, 2001. 142 pp, ISBN 085404-652-6, £9.95. reviewed by Richard Pagni
If there is one area in which the average organic chemist’s knowledge is deficient, it probably is the chemistry of heterocyclic compounds. This is, on reflection, surprising because the subject is vast and of paramount importance to biological chemistry. There are currently 80 volumes in Advances in Heterocyclic Chemistry, and dozens of books and monographs and at least two journals on the subject. Because there are so many things that an organic chemist needs to learn, some things are inevitably missed. As with so much of science these days, the subject primarily belongs to specialists. What is one to do to rectify this deficiency? For the already too busy academic or industrial chemist, there is perhaps little time to master a new subject. For a graduate or advanced undergraduate student there is hope, however. They can begin their exploration of heterocyclic chemistry with the book under consideration, Heterocyclic Chemistry, in a course with the same name. Malcolm Sainsbury, an expert in the field and author of hundreds of papers, has written a book on heterocyclic chemistry which, in the author’s own words, will “meet the needs of undergraduate students.” To keep the subject matter in reasonable bounds, the author has restricted the discussion to rings containing only one heteroatom. The book, volume 8 in The Royal Society of Chemistry’s tutorial chemistry series, consists of eight chapters, all approximately of the same length. The coverage includes pyridine and benzopyridines, pyrylium and benzopyrylium salts, pyrrole, furan, and thiophene and their benzo derivatives, four-membered heterocycles, and several other heterocycles. Each chapter is organized in the same manner. The aims and coverage are presented first. This is followed by an extensive discussion of the chemistry that is liberally sprinkled with clear, well-drawn structures and equations that
are given in boxes and schemes. The author’s use of arrow notation here, I might add, is impeccable. There are also two or three worked out problems within the chapter and numerous margin notes that provide useful information that would be disruptive if placed in the narrative. Near the end of the chapter there are additional problems whose answers may be found at the back of the book. A summary of pertinent points, references, and a list of books for further reading conclude the chapter. One gets a feeling for what is contained in a chapter by looking at the one on pyridine, a chapter I particularly enjoyed. It opens with a short description of the resonance picture of pyridine. A nice, terse discussion of electrophilic aromatic substitution follows. You may be surprised to learn that many of these reactions occur by addition–elimination mechanisms. After a consideration of the synthesis and chemistry of the fascinating pyridine N-oxide, there is discussion of nucleophilic aromatic substitution including those involving pyridynes (i.e., didehydropyridines). After a half-page on lithium–halogen exchange reactions, there is a detailed description of the most useful procedures for the synthesis of pyridines. The chapter concludes with a discussion of common pyridines including the picolines (methylpyridines), and reduced pyridines including the biologically important NADH+. As you can see, there is a wealth of material packed into fewer than 24 pages. The book, in my opinion, is very readable and quite suitable for use in a senior-level course. It is also remarkably free of errors of all kinds. The narrative is very concise, a drawback no doubt to some. Although the author does a good job in giving background material, there are a (very) few places where there are misplaced assumptions of what an advanced undergraduate student, particularly an American one, should know. How many seniors know what a retrosynthetic analysis is, for example? All in all this is a very fine textbook that a teacher planning to offer an undergraduate course in heterocycle chemistry should consider adopting. Richard Pagni is in the Department of Chemistry, The University of Tennessee, Knoxville, TN 37996-1600;
[email protected].
JChemEd.chem.wisc.edu • Vol. 79 No. 9 September 2002 • Journal of Chemical Education
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