Selective Nitration of Open-Cage [60]Fullerene Derivatives by Ponzio Reaction

The carbonyl group on the rim of open-cage C-60 derivative was converted into an oxime group when treated with hydroxylamine. Nitrogen tetroxide could convert the oxime group into gem-dinitro groups, similar to the Ponzio reaction of classical organic compounds. Single crystal X-ray diffraction data shows that one of the nitro group is directly above the orifice acting as an effective stopper. Presence of the gem-dinitro groups also showed significant effect on the reactivity of other functional groups on the rim of the orifice.

Automated summary

The study found that the open-cage C-60 derivative can be converted into a compound with gem-dinitro groups through a series of chemical reactions, and the presence of nitro groups has a significant impact on its reactivity.