Iron Porphyrin Catalyzed Oxidation of Lignin Model Compounds. Oxidation of Phenylpropane and Phenylpropene Model Compounds
Cui F. and David Dolphin
Can. J. Chem.
The oxidation. of 1-(4-ethoxy-3-methoxyphenyl)propane (I) and 1-(4-ethoxy-3-methoxyphenyl)propene (II) by meso-tetra(2,6-dichloro-3-sulfonatophenyl)porphyrin Fe chloride (III) and tert-Bu hydroperoxide (t-BuOOH) are discussed. In addition to a Cαhydroxylation product, demethoxylation and direct aromatic ring cleavage products were found in the oxidation of I. When II was oxidized by III and t-BuOOH in aqueous acetonitrile, an acetonitrile-incorporated product was found. A mechanism for the oxidation of II is proposed.