Electrolytic Reduction of Naphthalene in Various Alcohol-Hexamethylphosphoramide Systems

Abstract

Abstract The electrolytic reduction of naphthalene was carried out in various alcohol-hexamethylphosphoramide (HMPA) systems in the presence of lithium chloride. The reduction of naphthalene proceeds effectively at relatively low cathode potentials in the presence of HMPA; the composition of the products varies with the changes in the reduction potential, the kind of alcohols, and the concentration of HMPA. The dark blue color is observed at the cathode during the electrolysis in HMPA solutions in either the presence or the absence of ethanol. It is suggested that the color reflects the generation of solvated electrons, and that reduction of naphthalene is caused not through a direct electron-transfer from the cathode, but through a reaction with solvated electrons as the reductive agent.