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.
