Ishikawa reagent

The active species is the hexafluoropropylamine; any enamine is converted into this by the hydrogen fluoride byproduct as the reaction proceeds.

It is an improvement on Yarovenko's reagent, the adduct of chlorotrifluoroethylene and diethylamine, which must be prepared in a sealed vessel and once prepared keeps only for a few days, even in the refrigerator.

The reagent is mostly used to convert primary alcohols to alkyl fluorides under mild conditions with high yield.

However, secondary and tertiary alcohols give a substantial amount of alkenes and ethers as side products.

The compound is prepared by adding hexafluoropropene to a solution of diethylamine in ether at 0 °C and distilling the product in vacuo.