The 2-fluorotosylates react with organomagnesium compounds and lead to the products where OTs is substituted by organomagnesium alkyl group. When the fluorine atom of 2-fluorotosylates is benzylic, elimination of FOTs is observed. In the case of cyanide ion as reagent, the formation of dinitriles (substitution of F and OTs by C≡N) or unsaturated nitriles (substitution of OTs and elimination of HF) is observed. Methanolysis of unsaturated nitriles occurs when the reaction is carried out in methanol.
A. Hedhli, A. Baklouti