ChemInform Abstract: N‐HALOGEN‐TRIFLUORMETHANSULFONSAEUREAMIDE

Abstract

Das Sulfonsäureamid (II) läßt sich mit F, in Gegenwart von KF + NaF bei ‐65°C zum N,N‐difluoramid (I), mit C12 in wäßrigem NaOH bei ‐10°C zum N,N‐Dichloramid (IID oxidieren.

Trifluoromethanesulfonamides and Related Compounds

“…In the same work, N,N-dichlorotriflamide was first synthesized in 55% yield by saturation of the alkaline solution of triflamide with chlorine upon cooling. 56…”

“…CF SO NCl However, the authors failed to obtain the corresponding N,Ndibromo derivative by the reaction of triflamide with hypobromous acid or by the reaction of the disodium salt of triflamide with bromine. 56 N,N-Dichlorotriflamide turned out to be a highly reactive species in various reactions. In a series of works, Rozentsveig et al have shown it to react with 1,2-dichloroethylene, 57−59 trichloroethylene, 58,60 , triflamide, acrylamide), and C-nucleophiles (phenol, thiophene, indoles, pyrazoles).…”

“…75 With nitrosobenzene, N,N-dichloro-(perfluoroalkane)sulfonamides give N,N-perfluoroalkanesulfonyl, N′-phenyldiazene N′-oxides. 76 "Chloramine-Tf", CF 3 SO 2 NNaCl, 56 was used by us for oxidative imination of a series of organosilicon sulfides. 77,78 Thus, it reacts with ethyl(trimethylsilyl)sulfide in dry methylene chloride in the presence of Et 3 BnN + Cl − to afford S-(trimethylsilylmethyl)-S-ethyl-(N-triflyl)sulfimide in 60% yield.…”

“…Triflamide is fluorinated with fluorine/nitrogen gas mixture in the presence of NaF/KF fusion at −65 °C to give N , N -difluorotriflamide in 33% yield . The product is a pale-brown gas, explosive on impact or heating; below 10 °C it is condensed into a colorless liquid. CF 3 SO 2 NH 2 → − 65 .1em ° normalC normalF 2 / normalN 2 CF 3 SO 2 NF 2 …”

“…In the same work, N , N -dichlorotriflamide was first synthesized in 55% yield by saturation of the alkaline solution of triflamide with chlorine upon cooling CF 3 SO 2 NH 2 → − 10 .1em ° normalC aq . .25em NaOH , .25em Cl 2 CF 3 SO 2 NCl 2 However, the authors failed to obtain the corresponding N , N -dibromo derivative by the reaction of triflamide with hypobromous acid or by the reaction of the disodium salt of triflamide with bromine …”