N. Weinberg, B. Belleau
1973
Citations
0
Influential Citations
30
Citations
Journal
Tetrahedron
Abstract
Abstract Anodic oxidation of benzenoid aromatic ethers in methanolic KOH soln at a platinum electrode constitutes a one step method for the synthesis of the rare class of compounds, herein designated as the quinone diketals. The mechanism of conversion of 1,4-dimethoxybenzene to the diketal of p-benzoquinone, based on the evidence accumulated, is considered to proceed via discharge of the adsorbed aromatic compound, followed by nucleophilic reaction of the solvent system with the electrogenerated cationic species. The quinone diketal products resulting from anisole, 1,4-, 1,2-, and 1,3-dimethoxybenzene, 9,10-dimethoxyanthracene and benzodioxane have been established. In contrast methyl benzoate, anisonitrite, and benzene were found to be unreactive in agreement with a direct discharge scheme which does not involve methoxy radicals.