Applications of high-potential quinones. Part 14. Oxidation of 4-hydroxy-3-methoxyphenylpropan-2-one and related compounds by dichlorodicyanobenzoquinone

Abstract

Oxidation of guaiacylacetone (3) by dichlorodicyanobenzoquinone in the inert solvent dioxan gives a polymer (7)′ together with small amounts of a dimer (5). In methanol, benzylic monomethoxy- and dimethoxy-derivatives (20) and (23) are formed. Evidence for the involvement of radical and quinone methide intermediates in the formation of these products is discussed. In the mass spectra of the monoalkoxy adducts, the characteristic fragmentation is loss of an acetyl group from the side-chain.