Abstract

Spiromethanofullerenes 5, 8 and 10 containing a nitrophenyl substituent attached to the methano adduct, were synthesized via the diazomethane route or via the Bingel reaction. The electrochemistry and electrolysis of these compounds were investigated in THF. Reductive electrolysis leads to the removal of the addend, formation of [60]fullerene, and to the formation of bis-adducts from the mono-adducts. The extent of the retro-cyclopropanation reaction varied as a function of the structural and electronic differences between the compounds. Electron spin resonance studies (ESR) allowed the observation of spin localization on the fullerene core or on the nitrobenzene moiety upon successive reductions.