N-(2-Tetrafluoro(trifluoromethyl)-λ⁶-sulfanyl(CF₃SF₄)-ethyl) Amines: The Influence of the CF₃SF₄ Group on Lipophilicity and pKa

Abstract

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 pKa 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.