Competition between C- and O-alkylation reactions in 5-nitroimidazole series: Influence of nucleophile

The new reductive alkylating agent, 2-(4-chloromethylstyryl)-1-methyl-5-nit ro-1H-imidazole gives exclusively O-alkylation with 2-nitropropane anion. T he electron-transfer C-alkylation is observed with the anions of ethyl 2-ni tropropionate and dialkyl alpha-substituted malonates. The competition betw een C- and O-alkylation reactions depends on the nature of the nucleophile because of the low rate of decomposition of the radical anion of the alkyla ting agent.