The electrochemical reduction of succinimide : Reactivity of quaternary ammonium ions under electrolysis conditions

A solution of succinimide in ether acetonitrile or N, N-dimethylformamide containing tetra-n-butylammonium fluoborate shows a single, irreversible reduction wave at a platimum cathode by cyclic voltammetry. Coulometry demonstrates that a single electron is transferred. The reaction is accompanied by the evolution of hydrogen at a rate such that the passage of one Faraday of charge results in the generation of almost exactly 0.5 mole of hydrogen. The product of these reactions is the succinimide anion which is stable in the electrolysis solution, but reacts with tetra-n-butylammonium ion during vpc analysis or in refluxing N, N-dimethylformamide to form N-n-butylsuccinimide.