Electrochemical Oxidation of Benzophenone Hydrazones

Article abstract of DOI:10.1021/jo00166a006

The anodic oxidation of benzophenone hydrazones (1) was found to give several products, depending upon the electrolysis conditions employed such as electrode material, temperature, and electrolyte composition.For example, the oxidation using a platinum anode at room temperature in LiClO4-MeCN afforded exclusively benzophenone azines (2), whereas in NaOMe-MeOH benzophenone dimethyl acetals (3) were formed as the main products.On the other hand, the oxidation using a graphite anode in refluxing MeOH containing NaOMe gave diphenylmethyl methyl ethers (4), along with diphenylmethanes (5).When the analogous electrolysis was conducted in the presence of methacrylic acid derivatives, corresponding diphenylcyclopropanes (7) were obtained in relatively high yields.