Regioselective synthesis of novel e-edge-[60]fullerenylmethanodihydropyrroles and 1,2-dihydromethano[60]fullerenes

Authors

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 WollongongFollow
Stephen G. Pyne, University of WollongongFollow

RIS ID

11992

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.

Abstract

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.