Condensation Mechanisms of Benzylchloride

Abstract

Benzylchloride condenses slowly to dimer or trimer by heating without catalysts. The mechanisms, especially the positions of condensation have been investigated using both the deuterium tracer technique and the infrared absorption method. The reaction occurs at the benzene ring ca. 40% and the rest at the side chain. The relatives of three positions of the ring are 1.0, 0.26 and 0.18 for para, ortho and metha, respectively. No evidence is found for isotopic effect on the condensation at the benzene ring. The cathionoide mechanisms are proposed.