Structural reassignment of the mono- and bis-addition products from the addition reactions of N-(diphenylmethylene)glycinate esters to [60]fullerene under bingel conditions

Abstract

The addition of N-(diphenylmethylene)glycinate esters (Ph 2C=NCH2CO2R) to [60]fullerene under Bingel conditions gives [60]fullerenyldihydropyrroles and not methano[60]-fullerenyl iminoesters [C60OC(CO2R)(N=CPh2)] as previously reported. Unequivocal evidence for the structure of C60C(CO 2-Et)(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. © 2005 American Chemical Society.