Reactivity and structure of alkyl vinyl ethers. Part II. Kinetics and mechanism of acid-catalysed hydrolysis

Abstract

The hydrolysis of a number of alkyl vinyl ethers has been studied in a series of aqueous organic solvents. The reactions are acid-catalysed and the reactivity of ROCHCH₂ falls in the sequence R = Bu^t, > Prⁱ, > Et, > Me. It is suggested that the transition state for acid-catalysed hydrolysis involves interaction of a proton with both the oxygen atom and the terminal methylene group. The reactivity towards hydrolysis is correlated with nuclear magnetic resonance and infrared spectroscopic investigations of these compounds.