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Structural re-assignment of the mono- and bis-addition products from the addition reactions of N-(diphenylmethylene)glycinate esters to [60]fullerene under Bingel conditions
Faculty of Science - Papers (Archive)
  • Graham E Ball, University of New South Wales
  • Glenn Ashley Burley, University of Wollongong
  • Leila Chaker, University of Wollongong
  • William Hawkins, University of Wollongong
  • James Williams, University of Wollongong
  • Paul A Keller, University of Wollongong
  • Stephen G Pyne, University of Wollongong
RIS ID
11970
Publication Date
1-1-2005
Publication Details

Burley, G., Chaker, L., Hawkins, W., Williams, J., Keller, P. A., Pyne, S. G. & Ball, G. (2005). Structural re-assignment of the mono- and bis-addition products from the addition reactions of N-(diphenylmethylene)glycinate esters to [60]fullerene under Bingel conditions. The Journal of Organic Chemistry, 70 8572-8574.

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.

Citation Information
Graham E Ball, Glenn Ashley Burley, Leila Chaker, William Hawkins, et al.. "Structural re-assignment of the mono- and bis-addition products from the addition reactions of N-(diphenylmethylene)glycinate esters to [60]fullerene under Bingel conditions" (2005) p. 8572 - 8574
Available at: http://works.bepress.com/pkeller/26/