Regioselective synthesis of [60]fullerene eta 5-indenide R3C60- and eta 5-cyclopentadienide R5C60- bearing different R groups

Treatment of a 1,7-diorgano60]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.