Cathodic Birch Reduction of Methoxyaromatics and Steroids in Aqueous Solution

Article abstract of DOI:10.1021/jo00171a011

The electroreduction of methoxybenzene, 1,2,3,4-tetrahydro-6-methoxynaphthalene, and several aromatic steroids using aqueous tetrabutylammonium hydroxide solutions is described.The reactions proceed in high yields, and the corresponding dihydro products are formed.Temperature and electrolyte concentration were found to have a strong effect on the reaction rate.A direct electron transfer to the aromatics is unlikely, and a possible reduction mechanism involving the intermediacy of tetrabutylammonium amalgam is proposed.