72054-78-5Relevant academic research and scientific papers
Anodic Oxidation of 1,4-Dimethoxy Aromatic Compounds. A Facile Route to Functionalized Quinone Bisketals.
Henton, Daniel R.,McCreery, Richard L.,Swenton, John S.
, p. 369 - 378 (2007/10/02)
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.
Chemistry of Quinone Derivatives. Quinone Monoketals via Hydrolysis of Electrochemically Derived Quinone Bisketals
Henton, Daniel R.,Anderson, Keith,Manning, Michael J.,Swenton, John S.
, p. 3422 - 3433 (2007/10/02)
The monohydrolysis of nine naphthoquinone bisketals and nine benzoquinone bisketals has been studied.In the acetamido, bromo, methyl, methoxy, and thiomethyl monosubstituted compounds, hydrolysis occurs at the ketal more distant from the substituent.The regiochemistry is nearly exclusive in the naphthoquinone series and is highly selective in the benzoquinone series.For disubstituted benzoquinone and naphthoquinone bisketals, the monohydrolysis is often regiospecific but substituent dependent.The origin of the regioselectivity in the reactions is briefly discussed.
