BIOMIMETIC HYDROXYLATION OF AROMATIC COMPOUNDS: HYDROGEN PEROXIDE AND MANGANESE-POLYHALOGENATED PORPHYRINS AS A PARTICULARLY GOOD SYSTEM.

Article abstract of DOI:10.1016/S0040-4039(00)97136-3

Various iron- and manganese-porphyrins were compared as catalysts for the hydroxylation of anisole by H2O2 or PhIO.Whereas all the iron-porphyrins tested gave low hydroxylation yields, Mn(III)-meso-tetraarylporphyrins bearing halogen substituents on their meso-aryl and pyrrole groups gave good yields (up to 70percent based on the oxidant) for the para-hydroxylation of anisole, especially with H2O2 as oxidant in the presence of imidazole.Under these conditions, phenanthrene was quantitatively oxidized into its 9,10-epoxide and naphthalene was mainly oxidized into 1-naphthol (40percent yield).Hydroxylation yields appeared dependent upon the reactivity of the oxidizing system not only toward the starting aromatic compound but also toward the phenol products.