Evaluation of catalytic efficiency of a triple-site phase transfer catalyst and the kinetics of dichlorocarbene addition to 5-vinyl-2-norbornene

A new triple-site phase transfer catalyst viz., 1,3,5-tris(ethylmethyleneammonium bromide)-2,4,6-trimethyl benzene (TEMABTB) was prepared by the quaternization of 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene using triethylamine and its catalytic efficiency was ascertained by following the kinetics of dichlorocarbene addition of 5-vinyl-2-norbornene. Comparative catalytic activity of various onium salts (single-, di- and tri-site) have been investigated in detail. Based on the kinetic results obtained, a plausible mechanism has been proposed.