Synthesis of Fullerene Oxides Containing Both 6,6-Closed Epoxide and 5,6-Open Ether Moieties through Thermolysis of Fullerene Peroxides

Thermolysis of the fullerene hexaadduct C60(OOtBu)6 results in cleavage of two O−O bonds and elimination of two tert-butoxy groups to form two isomeric products with the formula C60(O)2(OOtBu)4 in comparable yields. The two oxygen atoms exist as two epoxy groups in one isomer 3, and as an epoxy and an ether group in the other isomer 2. Addition of hydroxylamine to 2 opens both the epoxy and the ether moieties to give a cage-opened keto-ketoxime derivative.