CATHODIC REDUCTION OF 1,2-DIBENZOYLCHLOROETHANE - FORMATION OF CYCLICDIMOLECULAR PRODUCTS

The electrochemical reduction of 1,2-dibenzoylchloroethane in aprotic medium (DMF-LiClO4) on mercury cathode gives four dimeric products. Tw o of them correspond to cyclic structures, 1-phenyl-c-2,t-3,c-4-triben zoyl-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 rac emic 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 fo rmation of furans, bisfurans, or cyclopentenes depending on the experi mental conditions.