Abstract 1-Methyl-2-chloromethyl-5-nitroimidazole reacts with tertiary nitronate anions in excess to afford in high yields the previously unknown 1-methyl-5-nitro-imidazoles bearing a trisubstituted ethylenic double bond in the 2 position. These compounds are ascribed to a C- alkylation reaction according to the S RN 1 mechanism followed by base-promoted nitrous acid elimination.