A number of reactions of endohedral metallofullerenes (EMFs) have been reported in the literature. Recently, we investigated the reaction of aryl azides with Sc₃N@I_h-C₈₀. It was found that isomeric [5,6]- and [6,6]-azafulleroids can be obtained from the thermal reaction of Sc₃N@I_h-C₈₀ with 4-isopropoxyphenyl azide, while photoirradiation leads exclusively to the [6,6]-azafulleroid.^[1] Surprisingly, when the thermal reaction was conducted at a lower temperature and under the aerobic conditions, an EMF isoxazoline derivative having a hexa-2,4-dienal moiety was obtained. This unprecedented reaction involved the aromatic ring scissoring and participation of O₂. The same phenomena were applied to the reaction of Sc₃N@I_h-C₈₀ with other electro-rich aryl azides.

References

1. Liu, T.-X.; Tao, W.; Zhu, S.-E; Wang, G.-W.; Jiao, M.; Yang, S.; Bowles, F. L.; Olmstead, M. M.; Balch, A. L. J. Am. Chem. Soc. 2012, 134, 11956-11959.