Isolation and characterisation of C-s-symmetry C60Me5O2OH, the first methylated fullerenol; a bis-epoxide with two oxygens in a pentagonal ring

From the reaction between [60]fullerene and MeLi, we have isolated C60Me5O2 OH, which has been characterised by both H-1 and C-13 NMR spectroscopy and by single-crystal X-ray analysis; uniquely, both epoxide groups bridge 5 : 6-bonds in the same pentagon.