Isolation and characterisation of symmetrical C60Me6, C60Me5Cl and C60Me5O2OH, together with unsymmetrical C60Me5O3H, C60Me5OOH, C60Me4PhO2OH, and C60Me12; fragmentation of methylfullerenols to C-58

Reaction of freshly prepared C60Cl6 (from chlorination of [60]fullerene by ICI in benzene) with methyllithium followed by hydrolysis and work-up including HPLC separation yields C-s symmetry C60Me6 (isostructural with C60Br6 and C60Cl6), together with unsymmetrical C60Me12 which is comprised of two of the motifs present in C60Me6 and must arise from the presence of a small amount of C60Cl12 in the C60Cl6. From the same reaction mixture we have also obtained C60Me5Cl [isostructural with C60Ar5Cl and C-60(OR)(5)Cl], hydroxyepoxides [C60Me5O2OH (symmetrical), C(60)Me5OOH and C60Me4PhO2OH (both unsymmetrical)] and unsymmetrical C60Me(5)O(3)H (a cage-opened ketone). The results provide further information concerning the addition patterns and mechanistic features or fullerene chemistry, show that methylated. arylated, alkoxylated and halogenated [60]fullerenes are isostructural, and that C60Cl6 also contains traces of C60PhCl5. Some of the compounds give exceptionally high intensities of the C-58(+) fragmentation ion during El mass spectrometry