Naphthalene Oxidation by Peracetic Acid Catalysed by Mn(III) Porphine-like Complexes: Nature of Intermediates and Pathways of their Formation

Abstract

Mn ( III ) complexes of meso-tetra(o,o′-dichlorophenyl)porphyrin, tetra-tert-butyl-tetraazaporphine and 3,5-octanitrophthalocyanine are efficient catalysts of naphthalene oxidation by peracetic acid in acetonitrile solution. The pathways of the reaction and the nature of intermediates and final products depend on the catalyst structure. For meso-tetra(o,o′-dichlorophenyl)porphyrin MnCl and tetra-tert-butyl-tetraazaporphine MnCl the single primary oxidation product is 1-naphthol. For 3,5-octanitrophthalocyanine MnCl, two pathways of naphthalene oxidation yielding 1-naphthol (as the primary product) and 1,4-naphthoquinone are proposed. The pathway of 1,4-naphthoquinone formation in the 3,5-octanitrophthalocyanine MnCl -catalysed reaction seems to involve two intermediates, 1,4-endo-peroxy-1,4-dihydro- and 2,3-epoxy-1,4-endo-peroxy-1,2,3,4-tetrahydronaphthalene.