Chemical transformation of the dimeric dianion of 1,1-diphenylethylene

Abstract

The chemical behaviour of the dimeric dianion ^–CPh₂·CH₂·CH₂·Ph₂C^–(1) derived from 1,1-diphenylethylene was examined with the intention of using the regeneration of the initial alkene as a means of detecting one-electron transfer reactions. With alkyl halides, dihalogenoalkanes, benzaldehyde, ethyl chloroformate, ethyl chloroacetate, and methyl benzoate, the dianion (1) showed conventional nucleophilic substitution and addition reactions complicated by the formation of cyclic intermediates and products, by protonation reactions, and by hydride transfer reactions. Only with methylene iodide, 1,2-dibromoethane, and iodine was the evidence indicative of electron transfer reactions.