ChemInform Abstract: Preparation of Enantiomerically Pure C₇₆ with a General Electrochemical Method for the Removal of Di(alkoxycarbonyl)methano Bridges from Methanofullerenes: The Retro‐Bingel Reaction.

Abstract

Preparation of Enantiomerically Pure C 76 with a General Electrochemical Method for the Removal of Di(alkoxycarbonyl)methano Bridges from Methanofullerenes: The Retro-Bingel Reaction.-Electrochemical reduction of title methano-bridged C 60 , C 70 , and C 76 fullerenes at controlled potentials leads initially to their monoanionic state, which is fully reversible. Controlled potential electrolysis (CPE) at the second reduction potential leads to complete chemical irreversibility (retro-Bingel reaction) yielding the corresponding fullerenes. When the diastereomerically pure, optically active C 76 monoadducts are submitted to CPE the two enantiomers, C 76 and ent-C 76 are obtained in 5-10% yield. -(KESSINGER, R.; CRASSOUS, J.; HERRMANN, A.; RUETTIMANN, M.; ECHEGOYEN, L.; DIEDERICH, F.; Angew.