Electro-organic synthesis of dibenzylaminodioxocyclohexa-dienecarboxylic acids

Abstract

Electrochemical oxidation of dihydroxybenzoic acids 1a-c has been studied in the presence of dibenzylamine (3) as nucleophile in water/acetonitrile (90:10) solution using cyclic voltammetry and controlled-potential coulometry. The quinones 2a-c derived from dihydroxybenzoic acids participate in Michael addition reactions with dibenzylamine (3), and via ECE mechanism convert to the corresponding (dibenzylamino)dioxocyclohexadienecarboxylic acids 5a-c. © ARKAT.