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(CH2)(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.Chemistry, OrganicSCI(E)EIPubMed6ARTICLE52456-24627