Novel oxidation reactions of sterically demanding 3, 6-di-tert-butylporphyrin-o-quinones to muconic anhydride derivatives

M Speck, MO Senge, A Schäfer, H Kurreck

Index: Speck, Marcus; Senge, Mathias O.; Schaefer, Andreas; Kurreck, Harry Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 20 p. 2589 - 2592

Full Text: HTML

Citation Number: 9

Abstract

Porphyrin quinones with sterically demanding 3, 6-di-tert-butyl-o-quinones were synthesized for electron transfer studies. In the presence of atmospheric oxygen the covalently free base porphyrin-o-quinones are oxidized to muconic acid anhydride and 3, 6-dicarbonyl- derivatives. In contrast to the well established chemistry of catecholase models based on 3, 5-substituted quinones this is the first example for oxidative ring expansion of 3, 6- ...