P. Vanelle et al., FIRST ELECTRON-TRANSFER C-ALKYLATION INVOLVING A FUSED QUINONEIMIDAZOLE REDUCTIVE ALKYLATING AGENT, Tetrahedron letters, 35(20), 1994, pp. 3305-3308
The C-alkylation reaction of hydro-1-methyl-1H-naphtho[2,3-d]imidazol-
4,9-dione by 2-nitropropane anion is shown to proceed by the S(RN)1 me
chanism. This mecha,nism is confirmed by the inhibitory effects of dio
xygen, p-dinitrobenzene, cupric chloride and TEMPO.