Switch of electronic reactivity in fullerene C60: activation of three trans-4 positions via temporary saturation of the cis-1 positions.
[Structure: see text] The regioselective functionalization of C60 with a trans-4,trans-4,trans-4 trisaddition pattern is not feasible directly. We have found an indirect approach taking advantage of the modified electronic reactivity of cis-1 bisadducts. The cis-1 addition pattern electronically activates three trans-4 C=C bonds on the opposite hemisphere of C60, allowing further highly regioselective additions at these positions. Thermal removal of the cis-1 blocking unit results in a trans-4,trans-4,trans-4 trisadduct with C3v symmetry.
Chuang
Shih-Ching
SC
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Khan
Saeed I
SI
Rubin
Yves
Y
D018360:Crystallography, X-Ray; D004583:Electrons; D037741:Fullerenes / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013056:Spectrophotometry, Ultraviolet
D037741:Fullerenes; C069837:fullerene C60