Formation and characterisation of alkoxy derivatives of [60]fullerene

Abstract

Heating C₆₀Cl₆ with either methanol or propan-2-ol under reflux during 140 h yields 1,4-(MeO)₂C₆₀ and 1,4-(iPrO)₂C₆₀, respectively, the latter reaction being faster due to the greater nucleophilicity of propan-2-ol. The reaction between C₆₀Cl₆ and ROH–NaOR yields C₆₀(OR)₅Cl (R = Me, Et) both of which are isostructural with C₆₀Ar₅Cl. A by-product of the reaction with ethanol–sodium ethoxide is 1,4-(EtO)₂C₆₀ showing that chlorine elimination accompanies substitution; this parallels the formation of 1,4-Ph₂C₆₀ from the reaction between C₆₀Cl₆ and benzene–FeCl₃.