title: Reactivity of fullerene epoxide: preparation of fullerene-fused thiirane, tetrahydrothiazolidin-2-one, and 1,3-dioxolane.
abstract: 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.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
authors.forename: Xiaobing
authors.initials: X
authors.lastname: Yang
authors.forename: Shaohua
authors.initials: S
authors.lastname: Huang
authors.forename: Zhenshan
authors.initials: Z
authors.lastname: Jia
authors.forename: Zuo
authors.initials: Z
authors.lastname: Xiao
authors.forename: Zhongping
authors.initials: Z
authors.lastname: Jiang
authors.forename: Qianyan
authors.initials: Q
authors.lastname: Zhang
authors.forename: Liangbing
authors.initials: L
authors.lastname: Gan
authors.forename: Bo
authors.initials: B
authors.lastname: Zheng
authors.forename: Gu
authors.initials: G
authors.lastname: Yuan
authors.forename: Shiwei
authors.initials: S
authors.lastname: Zhang
mesh_terms: D018360:Crystallography, X-Ray; D004148:Dioxolanes / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D037741:Fullerenes / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004148:Dioxolanes; D004852:Epoxy Compounds; D037741:Fullerenes; D013440:Sulfides; D053778:Thiazolidines; C013523:ethylene sulfide; C010962:formal glycol