N -(2-Tetrafluoro(trifluoromethyl)-λ 6 -sulfanyl(CF 3 SF 4 )-ethyl) Amines: The Influence of the CF 3 SF 4 Group on Lipophilicity and p K a.

A practical synthetic path for the preparation of trans -CF 3 SF 4 -substituted amines has been described. Primary and secondary amines bearing a variety of different functional groups including amino acids, cyclic amines, and nucleosides were prepared. The desired amines were synthesized under mild conditions. The influence of the CF 3 SF 4 -group on the p K a and log D of a standard amine was established. The unusual conformation of the trans -CF 3 SF 4 -substituted tosylate has been verified via its crystal structure.