Aerobic oxidations of C60(2-) in the presence of PhCN and PhCH2CN: oxygenation versus dehydrogenation reactions.

Aerobic oxidations of dianionic C(60) were examined in PhCN and PhCH(2)CN, where dioxygen was activated to O(2)(•-) via the single-electron transfer from C(60)(2-) and underwent oxygenation and dehydrogenation reactions, respectively. Addition of PhCH(2)Br led to further benzylation for the oxygenated product but not for the dehydrogenated one, suggesting that the initial two negative charges were preserved for the intermediates of the oxygenation reaction but not for those of the dehydrogenation reaction.