Aerobic Oxidations of C₆₀^2– in the Presence of PhCN and PhCH₂CN: Oxygenation versus Dehydrogenation Reactions

Aerobic oxidations of dianionic C60 were examined in PhCN and PhCH2CN, where dioxygen was activated to O2•– via the single-electron transfer from C602– and underwent oxygenation and dehydrogenation reactions, respectively. Addition of PhCH2Br 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.