User:Adrianpip2000/sandbox
Sulfonyl fluoride
In organic chemistry, a sulfonyl fluoride is an organic compound with the functional group −S(=O)(=O)Cl. Their formula is usually written R−SO2F, where R is a side chain. They derivatives of sulfonic acids (R−S(=O)(=O)OH).
Stuff
Also see Sulfonyl halide#Sulfonyl fluorides:
Sulfonyl fluorides have the general formula RSO2F. "Most, if not all" industrially synthesized perfluorooctanesulfonyl derivatives, such as PFOS, have the sulfonyl fluoride as their precursor.[1]
In the laboratory, sulfonyl fluorides are used in molecular biology as reactive probes. They specifically react with residues based on serine, threonine, tyrosine, lysine, cysteine, and histidine. The fluorides are more resistant than the corresponding chlorides and are therefore better suited to this task.[2]
Some sulfonyl fluorides can also be used as deoxyfluorinating reagents, such as 2-pyridinesulfonyl fluoride (PyFluor) and N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor).[3][4]
References
- ^ Lehmler, H. J. (2005). "Synthesis of environmentally relevant fluorinated surfactants—a review". Chemosphere. 58 (11): 1471–1496. Bibcode:2005Chmsp..58.1471L. doi:10.1016/j.chemosphere.2004.11.078. PMID 15694468.
- ^ Narayanan, Arjun; Jones, Lyn H. (2015). "Sulfonyl fluorides as privileged warheads in chemical biology". Chemical Science. 6 (5): 2650–2659. doi:10.1039/C5SC00408J. PMC 5489032. PMID 28706662.
- ^ Nielsen, Matthew K.; Ugaz, Christian R.; Li, Wenping; Doyle, Abigail G. (5 August 2015). "PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent". Journal of the American Chemical Society. 137 (30): 9571–9574. doi:10.1021/jacs.5b06307.
- ^ Guo, Junkai; Kuang, Cuiwen; Rong, Jian; Li, Lingchun; Ni, Chuanfa; Hu, Jinbo (28 May 2019). "Rapid Deoxyfluorination of Alcohols with N‐Tosyl‐4‐chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor) at Room Temperature". Chemistry – A European Journal. 25 (30): 7259–7264. doi:10.1002/chem.201901176.