Binuclear iron(III) phthalocyanine(μ-oxodimer)/tetrabutylammonium oxone: a powerful catalytic system for oxidation of hydrocarbons in organic solution

Binuclear iron(III) phthalocyanine-(μ-oxodimer) complex was tested in catalytic oxygenation reactions of several hydrocarbons using tetrabutylammonium oxone as the oxidant in dichloromethane solution at room temperature. Results of the study demonstrate that this is an extremely powerful catalytic system for oxidative conversion of aromatic hydrocarbons (anthracene, 2-tert-butylanthracene, 2-methylnaphthalene, 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, indane, ethylbenzene, toluene, and benzene) to the respective p-quinones in high yields in 5–30 min. Under these conditions, adamantane is oxidized with 71% conversion after 10 min affording a mixture of 1-adamantanol, 2-adamantanone, 1-hydroxy-2-adamantanone, and 4-protoadamantanone.