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Reactivity of Fullerene Epoxide: Preparation of Fullerene-Fused Thiirane, Tetrahydrothiazolidin-2-one, and 1,3-Dioxolane

2008; American Chemical Society; Volume: 73; Issue: 7 Linguagem: Inglês

10.1021/jo7023587

1520-6904

Xiaobing Yang, Shaohua Huang, Zhenshan Jia, Zuo Xiao, Zhongping Jiang, Qianyan Zhang, Liangbing Gan, Bo Zheng, Gu Yuan, Shiwei Zhang,

Graphene research and applications

The epoxide moiety in the fullerene-mixed peroxide C60(O)(OOtBu)4 1 reacts readily with aryl isocyanates ArNCS (Ar = Ph, Naph) to form both the thiirane derivative C60(S)(OOtBu)4 and fullerene-fused tetrahydrothiazolidin-2-one. The reaction of 1 with trimethylsilyl isothiocyanate TMSNCS yields the isothiocyanate derivative C60(NCS)(OH)(OOtBu)4, the isothiocyanate and hydroxyl moieties of which could be converted to a fullerene-fused tetrahydrothiazolidin-2-one ring with alumina quantitatively. Treating 1 with BF3·Et2O yields the fullerene-fused [1,3,2]-dioxoborolane derivative C60(O2BOH)(OOtBu)4. In the presence of aldehyde or acetone, BF3·Et2O catalyzes the conversion of epoxide to fullerene-fused 1,3-dioxolane derivatives. The products are characterized by spectroscopic data. Two of the compounds are also characterized by single-crystal X-ray analysis.