Electrochemically induced Favorskii rearrangement. α,β-Unsaturated amides and esters in the electrochemical reduction of polyhaloketones

Abstract

Electrochemically reduced polyhaloketones react with amines and phenols affording the corresponding α,β-unsaturated amides and esters in moderate yields. The formation of α-iminoketones and α-diimines (main products of the chemical reaction) is completely avoided. The stereochemistry of the α,β-unsaturated products is independent of the nature of the nucleophiles and haloketones.