Action of Potassium Fluoride and DBU on β-Fluoro-γ,δ-unsaturated p-Toluenesulfonates: a Convenient Route to Conjugated 2-Fluoroalkadienes

Article abstract of DOI:10.1016/0040-4039(95)00783-9

Potassium fluoride reacts in triethyleneglycol (TEG) on β-fluoro-γ,δ-unsaturated p-tolunensulfonates to give 2-fluoroalka-1,3-dienes (HOTs elimination) and the corresponding difluorolefins (substitution of O-tosyl group by fluorine).S_N/E competition may be related to the structure of the starting tosylate.However, the exclusive formation of conjugated 2-fluoroalkadienes may be realized by using DBU at room temperature instead of KF.