Synthesis and Reactions of Perfluorobutanesulfonyl Hypohalites

Article abstract of DOI:10.1021/jo00338a006

Two new hypohalites, perfluoro-n-butanesulfonyl hypochlorite and hypobromite, are reported.The hypochlorite is prepared by the low-temperature reaction of ClF with the acid C4F9SO2OH.The hypobromite is prepared by reaction of the hypochlorite with bromine.The new compounds contain very electrophilic halogen atoms and exhibit reactions similar to the analogous trifluoromethanesulfonates, CF3SO2OX (X=Cl, Br).The new hypohalites exhibit somewhat greater stability than the trifluoromethanesulfonates but form analogous decomposition products.Characterization of the newcompounds is given along with several reactions with olefins and halides to yield a variety of new esters.