An investigation of the biphasic kinetics observed during the hydroxide ion-catalyzed hydrolysis of alkyl dithioesters

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Abstract
Kinetic evidence is presented for the establishment of an equilibrium, in dilute aqueous alkaline solutions, between alkyl dithioesters and a species I. The species I is formed cither by the extraction of a proton from, or by the addition of an hydroxide ion to, the dithioester. In the former case I would be an anion (probably an enethiolate) formed by the removal of a proton from the α-carbon atom, and in the latter case I would be a stabilized tetrahedral intermediate formed by the addition of an hydroxide ion to the thiocarbonyl carbon atom. It has not been possible, using kinetic evidence alone, to distinguish conclusively between these two possibilities. However, using the available evidence, arguments are presented in favor of I being an enethiolate anion.

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