RESUMO
The cross-metathesis reactions of trans-tetrafluoro(trifluoromethyl)-λ6-sulfanyl (CF3SF4)-containing olefins expand the repertoire of synthetic transformations of CF3SF4-substituted molecules. Treatment of a primary alkene and 3-CF3SF4-propene with a second-generation Hoveyda-Grubbs catalyst yielded the cross-metathesis product in good yield under very mild conditions (room temperature). CF3SF4-propene undergoes cross metathesis with substrates containing electron-withdrawing groups or electron-donating groups at room temperature or under dichloromethane reflux. The formation of the CF3SF4-propene homodimer and the utility of that dimer to undergo selective cross-metathesis reactions are described.
RESUMO
A practical synthetic path for the preparation of trans-CF3SF4-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 CF3SF4-group on the pKa and log D of a standard amine was established. The unusual conformation of the trans-CF3SF4-substituted tosylate has been verified via its crystal structure.