Preparation and characterisation of two [70]fullerene diols, C70Ph8(OH)2

Reaction of a CCl4 solution of C70Ph8 with air in the presence of light and [70]fullerene gives a bis-lactone C70Ph8O4 (44%), together with a 1,2-diol, C70Ph8(OH)(2), 19,26,33,37,45,49,53,63-octaphenyl-7,8,19,26,33,37,45,49,53,63- decahydro[70]fullerene-7,8-diol (40%), 1 of C-s symmetry. This latter is also produced from reaction of a dichloromethane solution of C70Ph8 with 18-crown-6 and KMnO4, together with another C-s symmetry diol, 2, two possible structures for which are proposed; both 1 and 2 are the first diols to be derived from [70]fullerene. Whereas 1 is very insoluble in most organic solvents (but dissolves in THF), 2 is readily soluble in many organic solvents such as toluene, benzene, chloroform, carbon disulfide, and THF The derivatives show appreciable differences in both their NMR spectra and their EI mass spectrometry fragmentation patterns.