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.
State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Graduate School of Chinese Academy of Sciences, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022, China.
Hui-Lei
HL
Hou
Xiang
X
Gao
D000097:Acetonitriles / Q000737:chemistry*; D018360:Crystallography, X-Ray; D037741:Fullerenes / Q000737:chemistry*; D006865:Hydrogenation; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*
D000097:Acetonitriles; D037741:Fullerenes; D009570:Nitriles; C006725:benzyl cyanide; C069837:fullerene C60; D010100:Oxygen