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The oxidation of 8-methoxypsoralen (2) with hydrogen peroxide and potassium superoxide catalyzed by 5,10,15,20-(2,4,6-trimethylphenyl)porphyrinatoiron(III) chlorides [Me12TPPFe(III)Cl] (1a) and 5,10,15,20-(2,6-dichlorophenyl)porphyrinatoiron(III) chlorides [Cl8TPPFe(III)Cl] (1b) in dichloromethane gives 6-formyl-7-hydroxy-8-methoxycoumarin (3) in moderate yields, whereas the oxidation of (2) with H2O2 catalyzed by 5,10,15,20-(2,6-dichlorophenyl)-beta-octahaloporphyrinatoiron(III) chlorides [Cl8betaX8TPPFe(III)Cl] (X=Cl, Br) (1c, 1d) gives specifically 5,8-dioxopsoralen (4) in moderate yields.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Formation of 6-Formyl-7-hydroxy-8-methoxycoumarin and 5,8-Dioxopsoralen by Reaction of 8-Methoxypsoralen with H2O2 and Potassium Superoxide (KO2) Catalyzed by Halogenated or Perhalogenated 5,10,15,20-Tetraarylporphyrinatoiron(III) Chlorides.