Hexachloro[60]fullerene, C60Cl6, was reacted with a mixture of ROH/H2O (R = Me, Et, n-Pr, (CH2)2C≡CH) to form both C60Cl(OH)(OR)4 and C60Cl(OR)5. Only the C60Cl(OH)(OR)4 were isolated with bulky alcohols, ROH (R = (CH2)3C≡CH, (CH2)4C≡CH). Tetrahydro[60]fullerene epoxides, C60(O)(OR)4, were prepared by treating C60Cl(OH)(OR)4 with CuI. The epoxy moiety could be hydrolyzed to the vicinal diol derivatives, C60(OH)2(OR)4, and then oxidized to form dicarbonyl open-cage fullerenes, C60O2(OR)4. CuI was found to convert the terminal alkynyl addends into iodoalkynyl addends on the C60 cage.