Electrochemical formation of dianions from unsaturated cyclophanes

Abstract

A series of [2.₄]cyclophanetetraenes and closely related compounds has been shown to undergo reversible two-electron reduction at a mercury electrode in dimethylformamide solution. The cyclophanes which contain a conjugated periphery of 4nπ-electrons, thus being formally antiaromatic hydrocarbons, form dianions of pronounced stability. A considerable degree of structural and geometrical variation is tolerated.