Oxidative Cleavage of Pyrocatechol at the meta‐Position; A Model Reaction for Cleavage by Pyrocatechol‐2,3‐dioxygenase?

Abstract

The first nonenzymatic meta‐cleavage of pyrocatechol 1 was achieved with KO2 in dimethyl sulfoxide. The unstable yellow 2‐hydroxymuconaldehyde acid 2 was converted into picolinic acid. Since 1 is not cleaved to give 2 under N2, O 2⊖ as well as O2 might participate in the reaction.