The reaction of fullerene C(60) with 4,6-dimethyl-1,2,3-triazine: formation of an open-cage fullerene derivative.
A thermal reaction of fullerene C(60) with 4,6-dimethyl-1,2,3-triazine (4) in o-dichlorobenzene gave azacyclohexadiene-fused fullerene derivative 5, by the reaction with intermediate azete 11, and then, after flash chromatography over SiO(2), open-cage fullerene derivative 6 having an eight-membered ring orifice on the C(60) cage. Compound 6 is assumed to be formed via addition of diradical intermediate 13 to C(60). Compound 6 underwent a further photochemical reaction with singlet oxygen with the cleavage of one of the double bonds at the rim of the orifice to afford triketone derivative 8 having a 12-membered ring orifice.
Murata
Y
Y
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
Murata
M
M
Komatsu
K
K
D002244:Carbon / Q000737:chemistry*; D002247:Carbon Isotopes; D016166:Free Radical Scavengers / Q000737:chemistry*; D037741:Fullerenes; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013816:Thermodynamics; D014227:Triazines / Q000737:chemistry*
D002247:Carbon Isotopes; D016166:Free Radical Scavengers; D037741:Fullerenes; D014227:Triazines; D002244:Carbon; C069837:fullerene C60