Reactivity in nucleophilic substitution. Part V. Solvolysis of diphenylmethyl toluene-p-sulphonate

Abstract

The methanolysis of diphenylmethyl toluene-p-sulphonate in 90% methanolic tetrahydrofuran has been studied kinetically. Reaction rates are increased linearly by addition of electrolytes such as lithium perchlorate, tetrabutylammonium perchlorate, and lithium toluene-p-sulphonate and the alpha deuterium kinetic isotope effect k_H/k_D= 1·11. These observations substantiate an S_N1 process for the methanolysis.