On the mechanism of succinyl transfer from aryl enolsuccinates to enolates of arylketones: addition–elimination vs. alkoxide-assisted retro-ene reaction

Abstract

The mechanism of succinyl transfer from aryl enolsuccinates to the enolates of aryl ketones has been studied by deuterium exchange experiments and semi-empirical calculations. The calculations indicate that direct elimination is favoured over the ene mechanism. The results of a deuterium labelling study were also inconsistent with the ene mechanism.