Generation of acyl anion equivalents by in situ cathodic reduction of acyl tributylphosphonium ions anodically generated from tributylphosphine and carboxylic acids: preparation of α-hydroxy cycloalkanones from keto acids

Abstract

The preparation of α-hydroxy cycloalkanones from keto acids was effectively achieved by constant current electrolysis in the presence of Bu₃P in an undivided cell under an N₂ atmosphere, where the α-oxy ylides generated by the in situ cathodic reduction of acyl tributylphosphonium ions, formed anodically from tributylphosphine and carboxylic acids, seems to function as a novel acyl anion equivalent.