Single-electron-transfer-initiated thermal reactions of arylmethyl halides. Part 11. The reaction of trityl halides with sodium methoxide in 2,2-dimethoxypropane

Abstract

Trityl chloride (1a) and bromide (1b) furnish with sodium methoxide in 2,2-dimethoxypropane, in addition to several minor products, mixtures of the substitution products methyl trityl ether (1c) and p-methoxytriphenylmethane (2a), and of the reduction products triphenylmethane (1f) and p-diphenylmethyltritylbenzene (3a) which are the products of competing S_N and single-electron-transfer-initiated processes. Compound (1c) is suggested to be formed via two successive S_N′ processes rather than by either the S_N1 or S_N2 mechanisms which are both disfavoured under the experimental conditions applied.