Anodic Oxidation of 1,4-Dimethoxy Aromatic Compounds. A Facile Route to Functionalized Quinone Bisketals.

Article abstract of DOI:10.1021/jo01291a001

The anodic oxidation of 12 functionalized 1,4-dimethoxybenzene derivatives and 8 functionalized 1,4-dimethoxynaphthalenes has been studied under a variety of conditions.Many substituted 1,4-dimethoxy aromatics afford high yields of the respective quinone bisketals by single-cell anodic oxidation without accurate control of the electrode potential.Oxidizable groups offen complicate the anodic oxidation; however, in some cases protected derivatives of these functionalities can be converted to the bisketals in good yields.Aromatics containing reducible functions can besmoothly oxidized to quinone bisketals by the use of a divided cell.The current efficiencies and the effect of electrode material on selected systems are reported and discussed.