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

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.