Selective synthesis of fullerenol derivatives with terminal alkyne and crown ether addends.
A series of isomerically pure alkynyl-substituted fullerenol derivatives such as C(60)(OH)(6)(O(CH(2))(3)CCH)(2) were synthesized through Lewis acid catalyzed epoxy ring opening and/or S(N)1 replacement reactions starting from the fullerene-mixed peroxide C(60)(O)(t-BuOO)(4). Copper-catalyzed azide-alkyne cycloaddition readily converted the terminal alkynyl groups into triazole groups. Intramolecular oxidative alkyne coupling afforded a fullerenyl crown ether derivative.
Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China.
Huan
H
Huang
Gang
G
Zhang
Sisi
S
Liang
Nana
N
Xin
Liangbing
L
Gan
D000480:Alkynes / Q000737:chemistry*; D043844:Crown Ethers / Q000737:chemistry*; D037741:Fullerenes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000480:Alkynes; D043844:Crown Ethers; D037741:Fullerenes; C108127:fullerenol