Reduction of tetraphenylallene and related compounds in aprotic solvents

Abstract

Electrochemical methods have been used to show that the radical anions of tetraphenylallene and tetraphenylpropene undergo rapid protonation under conditions in which the radical anions of planar aromatic hydrocarbons are stable. Further reduction occurs to the tetraphenylallyl carbanion which was identified by visible and electron spin resonance spectroscopy and chemical methods. Aspects of the reduction are discussed in terms of molecular orbital theory.