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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 edit
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 edit
References 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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