Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. XIII. Solvent Effect on Rearrangement Reaction of Allylic Xanthates and a Correction of the Former Report

Abstract

To provide an additional evidence which confirms the concerted mechanism postulated for the thermal rearrangement reaction of allylic xanthates, the kinetic study on the rearrangement of them was conducted in a variety of solvent. The rearrangement showed a first order process with relatively low sensitivity to the ionizing power of the medium indicating that it proceeds by a mechanism which involves very little change in charge separation between the ground state and the transition state. In addition, this paper includes the correction of the former report referring to the product formation in the thermolysis of cinnamyl S-methyl xanthate.