Electroorganic chemistry—XI : The stereochemistry of electroreduction of cyclic ketones

Cyclic ketones were electrolytically reduced in isopropanol and in H₂SO₄H₂OMeOH. It was found that, in isopropanol the stereoisomer ratios of the products were approximately equal to the thermodynamic relative stabilities, whereas in H₂SO₄H₂OMeOH the thermodynamically unstable epimeric alcohols formed were more than that anticipated from the relative stabilities. The mechanism of this electroreduction involving the stereoselective adsorption and electron transfer is discussed.