Action of base on non-enolisable carbonyl compounds. Part I. Cleavage of benzophenones and some related ketones

Abstract

The cleavages of a range of benzophenones (most of which are monosubstituted) with the reagent formed by adding water (3 equiv.) to potassium t-butoxide (10 equiv.) in 1,2-dimethoxyethane have been studied. The effects of substituents on the direction and rate of overall cleavage have been investigated. The results are rationalised in terms of a mechanism in which the cleavage step affords a benzoate anion and an aryl carbanion. The fate of the aryl carbanions has been determined.