Preparation and characterisation of unsymmetrical C60Ph4 and symmetrical C60Ph2: the effect of regioselective nucleophilic attack upon C60Cl6

Unsymmetrical C60Ph4 (1,3,11,30-tetraphenyl-1,3,11,30-tetrahydro[60]fullerene) is obtained as a minor product from the reaction of C60Cl6 with benzene–FeCl3. The formation of either this compound or the major product (C60Ph5Cl) apparently depends on the position of the initial replacement of chlorine by phenyl: substitution of chlorine at the 2-position leads to C60Ph5Cl, whereas initial substitution of chlorine at the 1-position leads to C60Ph4. A small amount of symmetrical C60Ph2 (which mechanistic considerations indicate to be the 1,4-isomer), is also obtained and is accompanied by traces of C60Ph3H3.