Aromatic hydroxylation. Part 7. Oxidation of some benzenoid compounds by iron compounds and hydrogen peroxide with the aromatic compound acting as substrate and solvent

Abstract

The oxidation of some monocyclic aromatic compounds, in the presence of tris(acetylacetonato)iron(III), with hydrogen peroxide has been investigated. The evidence presented suggests that the attacking species is the hydroxyl radical and that the mechanisms of these reactions, in which the aromatic compound serves as substrate and solvent, are very similar to those of the hydroxyl radical in aqueous solution. Thus benzene gives phenol and biphenyl, anisole gives phenol and methoxyphenols, and toluene gives a mixture of products from ring and sidechain oxidation. The oxidations can also be carried out using several other benzene-soluble iron compounds although benzene containing hexacyanoferrate-(II) and -(III), solubilised with Adogen 464, is stable to oxidations