First electron transfer C-alkylation involving a fused quinoneimidazole reductive alkylating agent

Article abstract of DOI:10.1016/S0040-4039(00)76892-4

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