Sulfamoyl fluoride
Sulfamoyl fluoride in organic chemistry is a functional group that has the chemical formula F-SO2-N(-R)-R'.
Examples include sulfamyl fluoride, where R, R' is H; difluorosulfamyl fluoride, where R and R' is F; dimethylsulfamoyl fluoride where R and R' is a methyl CH3 group; N-sulfinylsulfamoyl fluoride where R, R1 are replaced by a double bond to S=O; chloro(trifluoro-methyl)sulfamoyl fluoride where R=Cl and R' is trifluoromethyl CF3.
Others include bis(trifluoromethyl)-sulfamoyl fluoride; 1,2-hydrazinedisulfonyl fluoride (which is an inorganic dimer).
It can be contrasted with the sulfonimidoyl fluorides with structure R-S(O)(F)=N-R'.
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
- ^ 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 (24 June 2009). "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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