Solvent-Free Mechanochemical Reaction of [60]Fullerene with Phenylhydrazine Hydrochlorides

The solvent-free reaction of [60]fullerene with phenylhydrazine hydrochlorides 1a-e in the presence of sodium carbonate under high-speed vibration milling conditions afforded 1-aryl-1,2-dihydro[60]fullerenes 2a-e, amongst them 1- (4-nitrophenyl)-1,2-dihydro[60]fullerene 2e could not be obtained in the liquid-phase reaction. When excess sodium nitrite was employed to replace sodium carbonate, fullerotriazoline 3 was formed. Product 3 tended to decompose via the loss of molecular nitrogen to give azafulleriod 4.