Preparation and characterisation of unsymmetrical C(60)Ph(4) and symmetrical C(60)Ph(2): The effect of regioselective nucleophilic attack upon C60Cl6

Unsymmetrical C(60)Ph(4) (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 (C(60)Ph(5)Cl) apparently depends on the position of the initial replacement of chlorine by phenyl: substitution of chlorine at the 2-position leads to C(60)Ph(5)Cl, whereas initial substitution of chlorine at the 1-position leads to C(60)Ph(4). A small amount of symmetrical C(60)Ph(2), (which mechanistic considerations indicate to be the 1,4-isomer), is also obtained and is accompanied by traces of C60PH3H3.