Theoretical studies on nucleophilic vinylic halide substitution

The reactions of vinyl fluoride, chloride, bromide and iodide with CN^- and OH^- were studied. The trend of reactivity of vinyl halide with these two nucleophile is: fluoroethene<chloroethene ≈ bromoethene<iodoethene. The reaction of vinyl fluoride with CN^- tends to be a multi-step process while the reactions of the other three vinyl halides with CN^-, OH^- are all single-step processes. The nucleophilicity of CN^- is stronger than that of OH^-.