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

…, J Bassa, N Llado, R Pleixats

Index: Moreno-Manas, M.; Bassa, J.; Llado, N.; Pleixats, R. Journal of Heterocyclic Chemistry, 1990 , vol. 27, # 3 p. 673 - 678

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Citation Number: 23

Abstract

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.