Reactions of alkyl radicals. Part II. Reactions of alkylbenzenes with methyl radicals. Photolytic formation and reactions of ethyl and n-butyl radicals

Abstract

Several aromatic solvents have been alkylated using the photolysis of methyl-, ethyl-, and n-butyl-mercuric iodide as the sources of alkyl radicals. The relative proportions of nuclear and side-chain attack on toluene and on isopropylbenzene, and the distribution of the isomeric products of nuclear alkylation of toluene and of chlorobenzene are in agreement with the postulate that alkyl radicals are more nucleophilic than aryl radicals. The mechanism of formation of α-methylstyrene, as well as bicumyl, by side-chain attack on cumene is discussed.