Selective Synthesis of
Fullerenol Derivatives with
Terminal Alkyne and Crown Ether Addends
- Publication date
- Publisher
Abstract
A series of isomerically pure alkynyl-substituted fullerenol
derivatives
such as C<sub>60</sub>(OH)<sub>6</sub>(O(CH<sub>2</sub>)<sub>3</sub>CCH)<sub>2</sub> were synthesized through Lewis acid catalyzed epoxy
ring opening and/or S<sub>N</sub>1 replacement reactions starting
from the fullerene–mixed peroxide C<sub>60</sub>(O)(<i>t</i>-BuOO)<sub>4</sub>. Copper-catalyzed azide–alkyne
cycloaddition readily converted the terminal alkynyl groups into triazole
groups. Intramolecular oxidative alkyne coupling afforded a fullerenyl
crown ether derivative
