Lithiation of 1‐benzylimidazole. A hypothesis on the regioselectivity of the electrophilic attacks on the lithiated species

M. Moreno‐Mañas, J. Bassa, N. Lladó, R. Pleixats

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32 Citations (Scopus)

Abstract

Sequential lithiations of 1‐benzylimidazole, 1, and of 1‐benzyl‐1,2,4‐triazole, 2, followed by treatment with electrophiles others than alkyl halides result in reactions at C‐2. However, benzyl halides and, to a certain extent, iodomethane react at the N‐benzyl carbon atom. An explanatory hypothesis based on steric ortho effects is advanced. Copyright © 1990 Journal of Heterocyclic Chemistry
Original languageEnglish
Pages (from-to)673-678
JournalJournal of Heterocyclic Chemistry
Volume27
Issue number3
DOIs
Publication statusPublished - 1 Jan 1990

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