The Biomimetic Oxidation of β-1, β-O-1, β-5 and Biphenyl Model Compounds by Synthetic Iron Porphyrins
Cui, F. and David Dolphin
Bioorg. & Med. Chem.
Vol. 2, 7, 735-742
The degradation of 4 dimeric lignin model compounds by meso-tetra(2,6-dichloro-3-sulfonatophenyl)porphyrin FeCl is reported. 4-Ethoxy-3-methoxyphenylglycerol-β -guaiacyl ether (a β-O-4 dimer) was cleaved to give 4-ethoxy-3-methoxybenzaldehyde (I) and guaiacol as major products. The oxidation of 1-(4-ethoxy-3-methoxyphenyl)-2-(4-methoxyphenyl)-1,3-propanediol (a β-1 dimer) gave I, 4-methoxybenzaldehyde, and 4-methoxy-α-hydroxyacetophenone as major products. Side-chain oxidation and aromatic ring cleavage reactions occurred for the phenylcoumaran (α-5) model compound, Et dehydrodiisoeugenol. A biphenyl model compd., 4,4'-diethyldehydrodivanillin, was oxidized to give mono- and dicarboxy derivatives, as well as ring-cleaved products of the acid derivatives.