Lewis Acid Promoted Preparation of Isomerically Pure Fullerenols from Fullerene Peroxides C₆₀(OO<i>t</i>-Bu)₆ and C₆₀(O)(OO<i>t</i>-Bu)₆

Fullerene mixed peroxides C60(t-BuOO)6 and C60(O)(t-BuOO)6 react with Lewis acids to form various fullerenols through the partial fragmentation of t-BuOO groups. Two monohydroxyl fullerenols with the general formula C60(OH)(t-BuOO)5 and six monohydroxyl fullerenols with the general formula C60(O)(OH)(t-BuOO)5 were prepared, which are essentially the same except the location of the OH group. An additional reaction of the monohydroxyl fullerenols gave bis- and trishydroxyl fullerenols. Single-crystal X-ray structures have been obtained for the two monohydroxyl fullerenols. Other compounds are characterized by chemical correlation and their spectroscopic data. Cuprous bromide could protect the most reactive t-BuOO group from being attacked by stronger Lewis acids. The proposed mechanism mainly involves Lewis acid induced heterolysis of the peroxo O−O bond.