Regioselective synthesis of [60]fullerene η 5 -indenide R 3 C 60 − and η 5 -cyclopentadienide R 5 C 60 − bearing different R groups

Treatment of a 1,7-diorgano[60]fullerene with Grignard reagents or organocopper reagents affords a [60]fullerene indenide or a [60]fullerene cyclopentadienide regioselectively in good to excellent yields. These reactions gave an insight into the reaction mechanism of the organocopper penta-addition reaction of [60]fullerene, giving [60]fullerene cyclopentadienide in quantitative yield.