Chemical functional group
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 fluoridedimer )
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 (SO2 F2 ) or sulfuryl chloride fluoride (SO2 ClF). 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
^ 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 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 .
