In organic chemistry, sulfamoyl fluoride is an organic compound having the chemical formula F−SO2−N(−R1)−R2. Its derivatives are called sulfamoyl fluorides.

Examples of sulfamoyl fluorides include:

Derivative of F−SO2−N(−R1)−R2'R1R2
sulfamyl fluoride Hydrogen (H) Hydrogen (H)
difluorosulfamyl fluoride Fluorine (F) Fluorine (F)
dimethylsulfamoyl fluoride Methyl (CH3) Methyl (CH3)
N-sulfinylsulfamoyl fluoride Thionyl

(S=O)

 none
chloro(trifluoro-methyl)sulfamoyl fluoride Chlorine (Cl) Trifluoromethyl (CF3)
bis(trifluoromethyl)-sulfamoyl fluoride
1,2-hydrazinedisulfonyl fluoride
(an inorganic dimer)

Sulfamoyl fluorides are contrasted with the sulfonimidoyl fluorides with structure R1-S(O)(F)=N-R2.

Production

Sulfamoyl fluorides can be made by treating secondary amines with sulfuryl fluoride (SO2F2) or sulfuryl chloride fluoride (SO2ClF). Cyclic secondary amines work as well, provided they are not aromatic.[1]

Sulfamoyl fluorides can also be made from sulfamoyl chlorides, by reacting with a substance that can supply the fluoride ion, such as NaF, KF, HF, or SbF3.[1]

Sulfonamides can undergo a Hofmann rearrangement when treated with a difluoro-λ3-bromane to yield a singly substituted N-sulfamoyl fluoride.[2]

See also

References

  1. 1 2 Enders, Dieter (2014). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 40b: Amine N-Oxides, Haloamines, Hydroxylamines and Sulfur Analogues, and Hydrazines. Georg Thieme Verlag. p. 1286. ISBN 9783131721815.
  2. ↑ Ochiai, Masahito; Okada, Takuya; Tada, Norihiro; Yoshimura, Akira; Miyamoto, Kazunori; Shiro, Motoo (2009-06-24). "Difluoro-λ3-bromane-Induced Hofmann Rearrangement of Sulfonamides: Synthesis of Sulfamoyl Fluorides". Journal of the American Chemical Society. 131 (24): 8392–8393. doi:10.1021/ja903544d. PMID 19485369.


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