Regioselective Oxidation of Phenols Catalyzed by Polyphenol Oxidase in Chloroform

Article abstract of DOI:10.1021/ja00305a020

Mushroom polyphenol oxidase can catalyze the oxidation of a number of phenols to o-quinones in chloroform.While in water the enzymatic oxidation results in negligible yields due to rapid inactivation of the enzyme and spontaneous polymerization of the quinones, in chloroform a quantitative conversion has been achieved; the quinones produced have been nonenzymatically reduced to catechols, thereby affording a net regioselective polyphenol oxidase catalyzed hydroxylation of phenols.