The novel dimerisation of radical anions generated electrochemically in aqueous solution from maleimide

✍ Scribed by R.G. Barradas; S.L. Gust; J.D. Porter

• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 228 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82986-5

✦ Synopsis

The one-electron reduction of maleimide yields the novel compound 1,2,3,4-butane-tetracarboxylic 1,2:3,4 diimide exclusively. Substrate-substrate hydrogen bonding was found to have a profound influence upon the pathways and kinetics of this unusual reaction. Conjugated imides undergo facile electrochemical reduction in aqueous solutions. The kinetics and pH dependence of these reactions are consistent with electron transfer to an activated carbonyl group(1,2), but the overall course of the reactions may be atypical of electrochemical reduction of simple or conjugated carbonyl compounds. Reduction in acidic solution exemplifies this unique behaviour. Under these conditions, protonated carbonyl groups