Abstract
Concepts as well as matter exhibit the property of inertia. Truly new concepts meet an initial resistance proportional to their novelty, which, if it is overcome, converts to a powerful force directed at extending the idea far beyond its original sphere of applicability and appropriateness. Science is no less subject to this generalization than are the social sciences and humanities but has the obvious advantage of permitting—or rather requiring—the constant testing of its concepts against experimental fact. One of the best illustrations of such intellectual inertia in chemistry is found in the concept of reactive intermediates. Free radicals, carbanions, carbenes, and carbenium ions have all gone through this cycle of postulation, proof, overextension, and retrenchment. The consequences of this process are such modifications as radicaloids, complexed carbanions, carbenoids, and the “nonclassical ion problem.” The concept of the aryne intermediate has also followed this path albeit more recently and with less fanfare than some of its relatives. A central role in both the overextension and maturing of the aryne concept is played by five-membered hetarynes. It is the purpose of this chapter to critically examine this role through a detailed review of the postulation, preparation, and properties of five-membered hetarynes.
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References and Notes
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Reinecke, M.G. (1982). Five-Membered Hetarynes. In: Abramovitch, R.A. (eds) Reactive Intermediates. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-3192-6_5
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