One-pot synthesis of arylfluoroalkylsulfoxides and study of their anomalous 19F NMR behavior

Arylfluoroalkylsulfoxides were successfully synthesized in one-pot when fluoroalkylsulfinate reacted with benzene and triflic anhydride in triflic acid and dichloromethane as the medium. The characteristics of their 19F NMR spectra were examined and analyzed for these structures. Electronic and steric effects of substituents at α- or β-position were revealed to be the main cause of the anomalous behavior of their chemical shifts and coupling constants. Interactions between arylfluoroalkylsulfoxides and solvents were also investigated and discussed.

Arylfluoroalkylsulfoxides were successfully synthesized in one-pot when fluoroalkylsulfinate reacted with benzene and triflic anhydride in triflic acid and dichloromethane as the medium. The characteristics of their 19F NMR spectra were examined and analyzed for these structures. Electronic and steric effects of substituents at α- or β-position were revealed to be the main cause of the anomalous behavior of their chemical shifts and coupling constants. Interactions between arylfluoroalkylsulfoxides and solvents were also investigated and discussed.Figure optionsDownload as PowerPoint slide