The Dependence of the Mechanism of the Hydrolysis, Trans-esterification, and Trans-etherification of α,β-Alkenyl Ethers and Esters on Their Structure

New experimental data obtained in the study of the mechanism of the hydrolysis of ethers and esters formed by enols and the related trans-esterification and trans-etherification of these compounds are collected in the present review.
Recent studies have confirmed the early views that the hydrolysis of the ethers formed by enols passes through a stage involving hydration of the ethylene bond, have made it possible to describe this reaction scheme in considerable detail, and have shown that an analogous mechanism can be extended to the hydrolysis of the esters formed by enols, in the discussion of which, until recently, schemes involving nucleophilic substitution at the carbonyl group were used.
The large amount of data on the alkaline hydrolysis of enol acylates indicates that the mechanism of this reaction is similar to, but not identical with that of the alkaline hydrolysis of alkyl esters. 99 references.