Mechanism of hydrolysis of an unsymmetrical ketene O, O-acetal and of ketene O, S-acetals

R Hershfield, MJ Yeager, GL Schmir

Index: Hershfield,R. et al. Journal of Organic Chemistry, 1975 , vol. 40, # 20 p. 2940 - 2946

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Citation Number: 11

Abstract

The hydrolyses of an unsymmetrical ketene 0, O-acetal (2, 2-dichloro-l-ethoxy-l- phenoxyethylene, 1) and of two ketene 0, s-acetals [2, 2-dichlor0-l-ethoxy-l-ethylthioethylene (2) and 1-ethylthio-1-phenoxyethylene (3)] have been studied in acidic solution at 30'. The observed catalysis by hydronium ion and acetic acid, the deuterium solvent isotope effect (kH/kD= 3.0 with 3), and the nonlinear dependence of rate on buffer concentration at ...