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

Graham E Ball; Glenn A Burley; Leila Chaker; Bill C Hawkins; James R Williams; Paul A Keller; Stephen G Pyne

doi:10.1021/jo051282u

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

J Org Chem. 2005 Oct 14;70(21):8572-4. doi: 10.1021/jo051282u.

Authors

Graham E Ball¹, Glenn A Burley, Leila Chaker, Bill C Hawkins, James R Williams, Paul A Keller, Stephen G Pyne

Affiliation

¹ NMR Facility, School of Chemistry, University of New South Wales, Sydney, New South Wales 2052, Australia.

PMID: 16209611
DOI: 10.1021/jo051282u

Abstract

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.