Synthesis and Chemical Reactivity of Tetrahydro[60]fullerene Epoxides with Both Amino and Aryl Addends

2015-04-17T00:00:00Z (GMT) by Sisi Liang Liang Xu Liangbing Gan
Tetrahydro­[60]­fullerene epoxides C<sub>60</sub>(O)­Ar<sub><i>n</i></sub>(NR<sub>2</sub>)<sub>4–<i>n</i></sub>, <i>n</i> = 1, 2, have been prepared by treating 1,4-adducts C<sub>60</sub>(OH)­Ph and C<sub>60</sub>(Tol)<sub>2</sub> with cyclic secondary amines. The epoxy moieties in these mixed tetrahydro[60]­fullerene epoxides were hydrolyzed into the corresponding diol derivatives, which were further oxidized into diketone open-cage fullerenes with a 10-membered orifice. A few other reactions also showed that the present tetrahydro[60]­fullerene epoxides with both amino and aryl addends exhibit improved chemical reactivity over the tetraamino[60]­fullerene epoxide without any aryl group.