16. Regioselective Synthesis of Novel e-Edge-[60]fullerenylmethanodihydropyrroles and 1,2-Dihydromethano[60]fullerenes

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 bis-adducts under reductive conditions gave exclusively novel dihydromethano[60]fullerene derivatives. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)