FLUORIDE-ION AS A NUCLEOPHILE AND A LEAVING GROUP IN AROMATIC NUCLEOPHILIC-SUBSTITUTION REACTIONS

This paper analyzes the behaviour of the fluoride ion as a nucleophile and a leaving group in S(N)Ar reactions in the gas phase and in solution. Attention is focused on quantitative data relating to fluoride ion reactivity in S(N)Ar reactions relative to other halide ions and groups. The factors governing the regioselectivity of fluorine atom substitution in S(N)Ar reactions are discussed, as well as the synthetic consequences of such substitution.