Synthesis and reactions of fluoroalkanesulfonyl azides and N,N-dichlorofluoroalkanesulfonamides

Abstract

Thermolysis or photolysis of fluoroalkanesulfonyl azides R_FSO₂N₃ afforded the corresponding nitrene intermediates R_FSO₂N which reacted readily with alkanes, alkenes, benzene, dimethyl sulfide, dimethyl sulfoxide, pyridine and triphenylphosphine to give insertion or addition products. Similar results were obtained by the reactions of N, N-dichlorofluoroalkanesulfonamides, R_FSO₂NCl₂, with the same reagents in the presence of zinc powder. Treatment of R_FSO₂NCl₂ with alkene in the absence of zinc powder gave only a 1 : 1 adduct via a free-radical intermediate R_FSO₂NCl.