The benzilic ester rearrangement: synthesis of labelled compounds and theoretical studies

Abstract

1,3-Diphenyl-2(13C)-hydroxy-3-methoxypropan-1-one was synthesised and used to probe the mechanism of a benzilic ester rearrangement (BER). Computational studies suggest that the preferred site of attack of the nucleophile in this benzilic ester rearrangement is on C-14. On the basis of these results a new reaction mechanism is proposed.