Addition of diprotic nucleophiles to a C60–tetrazine monoadduct: structural reassignment and correction of a novel rearrangementElectronic supplementary information (ESI) available: select spectroscopic data for (±)-2, 3 and (±)-4. See http://www.rsc.org/suppdata/cc/b1/b104151g/

Abstract

C₆₀–tetrazine Diels–Alder adducts bearing electron deficient dihydropyridazine groups undergo chemoselective amination and hydration reactions upon addition of primary aliphatic amines and water, respectively, to form new adducts with 4,5-dihydropyrazole groups nested atop the [60]fullerene skeleton.