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

Authors

Graham E Ball, University of New South Wales
Glenn Ashley Burley, University of Wollongong
Leila Chaker, University of Wollongong
William Hawkins, University of WollongongFollow
James Williams, University of Wollongong
Paul A. Keller, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow

RIS ID

11970

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.