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Activity and selectivity in the electrophilic substitution of five-membered heterorings (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Data on the activity and selectivity in reactions involving the electrophilic substitution of five-membered heteroaromatic compounds with one heteroatom are discussed. Chief attention is directed to the reactions of pyrrole, furan, thiophene, and their substituted derivatives. The inconsistency in the change in the activity (reaction rate) — N>O>S — and in the positional selectivity (the α∶ß ratio) — N<S<O — that exists for all electrophilic substitution reactions in these systems is interpreted with allowance for the mechanisms of the reactions and the nature of the heteroatom.

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  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, 117913, Moscow

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1587–1605, December, 1980.

The author is grateful to Professors Ya. L. Gol'dfarb and N. S. Zefirov and I. A, Abron, V. A. Budylin, and A. P. Yakubov for their useful discussion of a number of the problems examined in this review. The author recalls with sincere gratitude the valuable advice he obtained from the prematurely deceased A. N. Kost in the preparation of this paper.

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Belen'kii, L.I. Activity and selectivity in the electrophilic substitution of five-membered heterorings (review). Chem Heterocycl Compd 16, 1195–1210 (1980). https://doi.org/10.1007/BF00501819

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