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Regioselective synthesis of novel e-edge-[60]fullerenylmethanodihydropyrroles and 1,2-dihydromethano[60]fullerenes
Faculty of Science - Papers (Archive)
  • Leila Chaker, University of Wollongong
  • Graham E Ball, University of New South Wales
  • James R Williams, University of Wollongong
  • Glenn A Burley, University of Wollongong
  • Bill C Hawkins, University of Wollongong
  • Paul A Keller, University of Wollongong
  • Stephen G Pyne, University of Wollongong
Publication Date
Publication Details

This article was originally published as: Chaker, L. Ball, GE, Williams, JR, et al, Regioselective synthesis of novel e-edge-[60]fullerenylmethanodihydropyrroles and 1,2-dihydromethano[60]fullerenes, European Journal of Organic Chemistry, December 2005, 2005(24), 5158-5162. Copyright 2005 John Wiley & Sons.

Treatment of a tethered N-(diphenylmethylene)glycinate-malonate derivative with [60]fullerene under Bingel conditions yielded an e-edge-[60]fullerenylmethanodihydropyrrole adduct in a regioselective manner. The regiochemical outcome was independent of the order of addition of either the N-(diphenylmethylene)glycinate or the malonate moieties. This new bis-adduct was also prepared in 13C enriched form allowing for its unequivocal structural characterization by 2D INADEQUATE NMR experiments. Ring-opening of the dihydropyrrole functionality of the bisadducts under reductive conditions gave exclusively novel dihydromethano[60]fullerene derivatives.
Citation Information
Leila Chaker, Graham E Ball, James R Williams, Glenn A Burley, et al.. "Regioselective synthesis of novel e-edge-[60]fullerenylmethanodihydropyrroles and 1,2-dihydromethano[60]fullerenes" (2005)
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