Aromatization reactions of 2-cyclohexenones and 1,3-cyclohexadien-1-amines with iodine/sodium alkoxide

2-Cyclohexenones containing an electron withdrawing group in the 4-position and the corresponding N-alkyl-1,3-cyclohexadien-1-amines undergo regioselective iodination and aromatization to give 2-iodophenols and N-alkyl-2-iodoanilines, respectively, upon reaction with iodine and sodium alkoxide. By contrast, N,N-dialkyl-1,3-cyclohexadien-1-amine derivatives undergo non-iodinative aromatization to simple N,N-dialkylanilines under similar conditions.