Reactivity of fullerene epoxide: Preparation of fullerene-fused thiirane, tetrahydrothiazolidin-2-one, and 1,3-dioxolane

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

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

(Chemical Equation Presented) 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·Et 2O yields the fullerene-fused [1,3,2]-dioxoborolane derivative C 60(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.

Original languageEnglish (US)
Pages (from-to)2518-2526
Number of pages9
JournalJournal of Organic Chemistry
Volume73
Issue number7
DOIs
StatePublished - Apr 4 2008

ASJC Scopus subject areas

  • Organic Chemistry

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