Selective Synthesis of Fullerenol Derivatives with Terminal Alkyne and Crown Ether Addends

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• 作者：Huan Huang ; Gang Zhang ; Sisi Liang ; Nana Xin ; Liangbing Gan
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：March 2, 2012
• 年：2012
• 卷：77
• 期：5
• 页码：2456-2462
• 全文大小：385K
• 年卷期：v.77,no.5(March 2, 2012)
• ISSN：1520-6904

文摘

A series of isomerically pure alkynyl-substituted fullerenol derivatives such as C₆₀(OH)₆(O(CH₂)₃CCH)₂ were synthesized through Lewis acid catalyzed epoxy ring opening and/or S_N1 replacement reactions starting from the fullerene鈥搈ixed peroxide C₆₀(O)(t-BuOO)₄. Copper-catalyzed azide鈥揳lkyne cycloaddition readily converted the terminal alkynyl groups into triazole groups. Intramolecular oxidative alkyne coupling afforded a fullerenyl crown ether derivative.