Base-induced instability of fluorotelomer alcohols

The stability of fluorotelomer alcohols under basic conditions was studied. HF elimination across the CF2–CH2 junction is shown to be facilitated by an intramolecular hydrogen bond, while solvation is the key determinant in the stability of alcohols of various perfluoroalkyl lengths. Finally, fluorotelomer alcohols can be rendered kinetically stable if either the alcohol or the base has low solubility in the reaction medium.