Book and Media Review pubs.acs.org/jchemeduc
Review of Heterocyclic Chemistry, 5th Edition Robert E. Buntrock* Buntrock Associates, Orono, Maine 04473, United States including those to the massive reference compendia of the field; a list of definitions of abbreviations is presented, and several chapters have exercises, with more available online.2 A reading sequence for undergraduates is also given. Hazards in reaction methods are noted but caution is given that these may not be comprehensive. Prior texts3−7 typically have been organized by discussion of ring systems from less to more complex (e.g., three-membered rings with one heteroatom, five-membered rings with two heteroatoms, etc.). Joule and Mills instead begin with more general topics, including comparisons of carbocyclic and heterocyclic aromaticity, tautomerism, spectral properties, ring syntheses, and typical reactivities. Subsequently, the chemistry of typical ring systems and classes of compounds within those systems is discussed. Following the general-to-specific philosophy, this book discusses nomenclature only in more general terms, followed by particular examples. This approach, a possible deficiency in the opinion of this reviewer, is opposite to the more systematic discussion of nomenclature in previous texts and compendia. Gilchrist4 has a quite detailed chapter on heterocyclic nomenclature. The latter approach enables correct naming of almost any heterocycle that may be encountered, including those with ring heteroatoms other than O, N, or S. However, references are given to comprehensive nomenclature resources. Within the text, common names are used and the CAS name, if different, follows in brackets. The reviewer was fortunate to have performed research in heterocyclic chemistry both as an undergraduate and a graduate student. I also took a course in heterocyclic chemistry from E. C. Taylor, an outstanding researcher and teacher. At that time only a few texts were available8,9 and Taylor taught primarily, but not exclusively, from the latter. Several additional texts have appeared since then (e.g., refs 3−7). Overall, this book is recommended as a text for undergraduate and more advanced students on this pervasive, important, and underappreciated topic in chemistry.
Heterocyclic Chemistry, 5th edition, by John A. Joule and Keith Mills. Wiley-Blackwell: New York, 2010. xxii + pp. ISBN: 978-1405193658 (paper). $59.95.
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y definition, heterocyclic compounds are cyclic compounds with at least one hetero (i.e., noncarbon) atom in the ring. The most common heteroatoms are oxygen, nitrogen, and sulfur, although other elements do participate. Why teach heterocyclic chemistry? Especially to undergraduates? Don’t you have more than enough to try to teach in a set amount of time? Well, in addition to the opinion of this “old” (in more ways than one) heterocyclic chemist, some relevant statistics are strongly suggesting that you do so. Estimates vary, but a probable majority of papers published in organic chemistry involve heterocyclic compounds. More than half of all natural products are heterocyclic. The majority of pharmaceuticals are heterocyclic small molecules. Their importance is significant, yet chemists’ background knowledge of heterocyclic compounds is often deficient.
Cover image provided by Wiley-Blackwell and reproduced with permission.
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Once you have decided to teach heterocyclic chemistry, what textbooks are available? Well, I would suggest this one. Aimed at undergraduates, covering the fundamentals of heterocyclic reactivity and synthesis, this book also includes enough more advanced material to be useful at higher levels. Improvements over the previous edition1 include the welcome use of color in reaction schemes for bonds and atoms undergoing change. Added chapters include those on organometallic heterocyclic chemistry, on more novel synthetic methods (solid state, microwave, and flow reactors), as well as on heterocycles in medicine, in biochemistry and as natural products, and on special topics (including bioprocessing, green chemistry, and ionic liquids). An entire chapter is devoted to saturated or partially unsaturated heterocycles, a topic sometimes ignored in reference works. There are more than 4000 references, © 2012 American Chemical Society and Division of Chemical Education, Inc.
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REFERENCES
(1) Joule, J. A., Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell: Oxford, U.K., 2000. (2) Instructor Companion Site for Heterocyclic Chemistry, 5th edition. http://www.wiley.com/go/joule (accessed Sep 2012). (3) Gupta, R. R.; Kumar, M.; Gupta, V. Heterocyclic Chemistry, Vols. I−III; Springer: Berlin, 1998. Published: September 14, 2012 1349
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Journal of Chemical Education
Book and Media Review
(4) Glichrist, T. L. Heterocyclic Chemistry, 3rd ed.; Longman: Harlow, England, 1997. (5) Newkome, G. R.; Paudler, W. W. Contemporary Heterocyclic Chemistry; Wiley: New York, 1982. (6) Paquette, L. A. Principles of Modern Heterocyclic Chemistry; W. A. Benjamin: New York, 1968. (7) Palmer, M. The Structure and Reactions of Heterocyclic Compounds; Edward Arnold: London, 1967. (8) Katritzky, A. R.; Lagowski, J. M. Heterocyclic Chemistry; Wiley: New York, 1960. (9) Albert, A. Heterocyclic Chemistry: An Introduction; Athlone: London, 1959.
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dx.doi.org/10.1021/ed300616t | J. Chem. Educ. 2012, 89, 1349−1350
