Fullerenyl azide: synthesis and reactivity

Trimethylsilyl azide adds to the carbonyl carbon in a cage-opened fullerene derivative to form the first fullerenyl azide compound. The fullerene-bound azido group exhibits some unusual reactivity compared with that exhibited by other organic azido compounds. Heating the azidofullerene at 100 °C only led to the cleavage of peroxo groups in the compound, whereas the azido group remained unchanged. Triphenylphosphine reacted with the azido group to form isolable iminophosphorane, which could not be hydrolyzed under normal acidic and basic conditions.