CYCLOPROPANE FORMATION BY ELECTROREDUCTIVE COUPLING OF ACTIVATED OLEFINS AND GEM-POLYHALO COMPOUNDS

Cyclopropyl derivatives have been prepared with satisfactory yields by electroreductive coupling of activated olefins and gem-polyhalo compo unds. The reaction is efficient when the olefin is more easily reduced than the organic halide. Two types of intermediates can be involved t o lead to the products. The radical anion of the olefin can react with the halo compound by electron-tranfer followed by radical coupling, o r be reduced into the dianion which reacts by nucleophilic displacemen t. (C) 1998 Elsevier Science Ltd. All rights reserved.