Abstract The C-alkylation reaction of 2-chloromethyl-3, 5, 6-trimethyl-1, 4-benzoquinone 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 di-tert- butylnitroxide. The dioxygen-induced formation of nitro and nitrite derivatives is found for the first time.