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

Abstract

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.