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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' | R1 | R2 |
|---|---|---|
| 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
editSulfamoyl 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
editReferences
edit- ^ a b 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.
- ^ 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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