Epoxide Dimers Formed Electrochemically from Phthalimide in Alkaline Solution: A Kinetic and Structural Analysis

The electrochemical reduction of phthalimide in alkaline solution was investigated in detail at a number of electrode surfaces. Two well‐separated electron transfer processes were observed and attention was focused on the first of these. The kinetic results indicated that a radical anion species was the initial product of this reaction and that the radicals so formed subsequently coupled rapidly in a classical solution‐dimerization reaction. Final product isolation and characterization were necessary to unambiguously assign the complete reaction pathway. The one‐electron reduction yielded an unusual epoxide dimer which contained five rings and two chiral spiro centers. The dl/ meso ratio of the product was 1.63.