ACYLATIONS OF PENTAFLUOROSULFANYLAMINE, SF5NH2. PART II. REACTIONS OF N-PENTAFLUOROSULFANYLCARBAMYLFLUORIDE, SF5NHC(O)F, AND N-PENTAFLUOROSULFANYLPERFLUOROSUCCINIMIDE,

Article abstract of DOI:10.1016/S0022-1139(00)83163-2

The carbamyl fluoride SF5NHC(O)F reacts with both H2O and H2S to give the urea (SF5NH)2CO.Evidence supports that this reaction proceeds through a mechanism involving dehydrofluorination; whereas, the reagents PhLi and PCl5 serve only to dehydrofluorinate SF5NHC(O)F.The ring of the cyclic imide can be readily opened by nucleophiles to give products such as SF5NHC(O)CF2CF2C(O)OH, SF5NHC(O)CF2CF2C(O)NH2, and SF5NHC(O)CF2CF2C(O)OCH3.Attempts to prepare analogous six- and seven-membered cyclic imides failed; however, mono- (SF5NHC(O)(CF2)3,4C(O)F) and disubstituted products (SF5NHC(O)(CF2)3,4C(O)NHSF5) were formed.The amide-acid fluorides are easily hydrolyzed by atmospheric moisture to the amide-acids SF5NHC(O)(CF2)3,4C(O)OH.