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

Tetrahydro­[60]­fullerene epoxides C₆₀(O)­Ar_<i>n</i>(NR₂)_4–<i>n</i>, <i>n</i> = 1, 2, have been prepared by treating 1,4-adducts C₆₀(OH)­Ph and C₆₀(Tol)₂ 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