[60]Fulleroindolines can accept two electrons to form the corresponding dianions, which involve the heterolytic cleavage of the C₆₀－N bond. The ring-opened structures are perfect building block for the further functionalizations. The synthesis of both tetrafunctionalized and hexafunctionalized products with unusual addition patterns have been achieved.^[1]

References

[1]. Xiao, Y.; Zhu, S.-E; Liu, D.-J.; Suzuki, M.; Lu, X.; Wang, G.-W. Angew. Chem. Int. Ed. 2014, 53, 3006-3010.