EPOXIDE DIMERS FORMED ELECTROCHEMICALLY FROM PHTHALIMIDE IN ALKALINE-SOLUTION - 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. © 1979, The Electrochemical Society, Inc. All rights reserved.