The kinetics and mechanism of the soft metal ion-promoted hydrolysis of α-ethoxy-α-ethylthiotoluene in aqueous solution

Abstract

Kinetic studies show that the overall hydrolysis of the open-chain OS-acetal α-ethoxy-α-ethylthiotoluene in aqueous solution, promoted by mercury(II) or by thallium(III) ions, proceeds via rapid desulphurisation to give the hemiacetal, followed by the rate-limiting hydrogen ion-catalysed hydrolysis of the latter. With mercury(II) ions, only in the presence of relatively high concentrations of added chloride ions does the mechanism change.