First Electron Transfer C-Alkylation Involving a Fused Quinoneimidazole Reductive Alkylating Agent.

The C-alkylation reaction of 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho[2,3-d]imidazol-4,9-dione by 2-nitropropane anion is shown to proceed by the SRN1 mechanism. This mechanism is confirmed by the inhibitory effects of dioxygen, p-dinitrobenzene, cupric chloride and TEMPO.