Cleavage of carbon–oxygen single bonds in the reaction of aryl ethyl acetals with ethylmagnesium bromide in diethyl ether. A kinetic study

Abstract

Acetaldehyde ethyl phenyl acetal and its p-methoxy-, p-methyl-, p-chloro-, and m-chloro-substituted derivatives were treated with ethylmagnesium bromide in diethyl ether. A substitution took place producing, after hydrolysis. phenols and ethyl s-butyl ether. Kinetic measurements were effected in the temperature range 0–40 °C. Second-order rate coefficients were correlated with Hammett σ values, giving ρ+ 2.35 (30 °C). The nucleophilic character of the reaction is discussed.