Heterogeneous reactions of copper(II) chloride with toluene, p-xylene, and mesitylene

Abstract

Treatment of boiling toluene with copper(II) chloride yields a mixture of phenyltolylmethanes, and not bibenzyl as previously reported. Similar treatment of p-xylene gives 4-tolyl-2,5-xylylmethane and 2-chloro-p-xylene, and mesitylene yields 2-chloromesitylene. The decomposition of copper(II) chloride obeys first-order kinetics. The reactions are interpreted in terms of formation of a radical cation by removal of an electron from the aromatic π-system.