Aromatic polyfluoro-compounds—XXXII: Isomer distributions in the nucleophilic replacement reactions of the pentafluorohalogenobenzenes

J Burdon, PL Coe, CR Marsh, JC Tatlow

Index: Burdon,J. et al. Tetrahedron, 1966 , vol. 22, p. 1183 - 1188

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Citation Number: 27

Abstract

The pentafluorohalogenobenzenes react with nucleophiles mainly at the position para to the halogen; ortho replacement occurs to a lesser extent and diminishes in the order C6F5Cl> C6F5Br> C6F5I∼ C6F5H. This is rationalized in terms of an electronic effect, which involves electron repulsion by halogens in π-electron systems and also by steric factors.