Aerobic Oxidations of
C<sub>60</sub><sup>2–</sup> in the Presence of PhCN and PhCH<sub>2</sub>CN: Oxygenation versus
Dehydrogenation Reactions
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Abstract
Aerobic oxidations of dianionic C<sub>60</sub> were examined
in
PhCN and PhCH<sub>2</sub>CN, where dioxygen was activated to O<sub>2</sub><sup>•–</sup> via the single-electron transfer
from C<sub>60</sub><sup>2–</sup> and underwent oxygenation
and dehydrogenation reactions, respectively. Addition of PhCH<sub>2</sub>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