alkylation3 of heterocycles by DMF acetals4 is well estab-lished. The absence of any acid catalyst, coupled with the observed nonregiospecific alkylation of the imidazole ring, suggests the intermediacy of the imidate cation 9 and the resonance-delocalized imidazole anion 10 in this reaction. All the starting materials employed in this investigation were prepared from the commercially available5 4 (5)-methylimidazole. Nitration6 of the latter ( ...
