15. Structural Reassignment of the Mono- and Bis-Addition Products from the Addition Reactions of N-(Diphenylmethylene)glycinate Esters to [60]Fullerene under Bingel Conditions

The addition of N-(diphenylmethylene)glycinate esters (Ph₂C_NCH₂CO₂R) to [60]fullerene under Bingel conditions gives [60]fullerenyldihydropyrroles and not methano[60]fullerenyl iminoesters [C₆₀C(CO₂R)(N_CPh₂)] as previously reported. Unequivocal evidence for the structure of C₆₀C(CO₂Et)(N_CPh₂) was provided by INADEQUATE NMR studies on ¹³C enriched material. New mechanistic details are proposed to account for the formation of [60]fullerenyldihydropyrroles and their reductive ring-opening reactions.