CATHODIC REDUCTION OF 1,2-DIBENZOYLCHLOROETHANE - FORMATION OF CYCLIC DIMOLECULAR PRODUCTS

The electrochemical reduction of 1,2-dibenzoylchloroethane in aprotic medium (DMF-LiClO4) on mercury cathode gives four dimeric products. Two of them correspond to cyclic structures, 1-phenyl-c-2,t-3,c-4-tribenzoyl-r-1-cyclopentanol (41-43%) and 1-phenyl-c-2,c-3,t-4-tribenzoyl-r-1-cyclopentanol (16-18%), and the other two were identified as the racemic and meso 1,6-diphenyl-3,4-dibenzoyl-1,6-butanediones (24-26 and 8-10%, respectively). The dehydration of these products leads to the formation of furans, bisfurans, or cyclopentenes depending on the experimental conditions.