An efficient acid hydrolysis of the ether bond assisted by the neighbouring benzamide group. Part 3

Abstract

The acid hydrolytic cleavage of 1 to 2, assisted by a neighbouring benzamide group, was kinetically investigated in a wide range of HCl concentrations (1.67–8.7 M) and at various temperatures. Kinetic measurements were performed also in the presence of LiCl at constant ionic strength (I = 5 M). The rate determining step of the acid hydrolysis of 1 was recognized through the investigation of the acid catalyzed cyclization of 3 to 2. Thermodynamic activation parameters were calculated and the experimental data discussed. The participation of the neighbouring benzamide group was evaluated to be about 7.3 × 10³.