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

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