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.
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.
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]