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2-Chloroethanesulfonyl chloride was used in one-pot sulfonylation/intramolecular thia-Michael protocol for the synthesis of 1,5,2-dithiazepine 1,1-dioxides. It was also used in synthesis of vinyl sulfonamides with a furan, carbocyclic, semi cyclic or acyclic 1,3-diene moiety.
James Frederick King; Kishan Chand Khemani. The mechanism of hydrolysis of 2-hydroxyethanesulfonyl chloride: the intermediacy of 1,2-oxathietane 2,2-dioxide (β-sultone). Canadian Journal of Chemistry. 1989, 67 (12), 2162-2172.
C. W. Huffman. Formylation of Amines. J. Org. Chem. 1958, 23 (5), 727-729.
In the presence of a base, converts alcohols to vinyl sulfonates: J. Am. Chem. Soc., 68, 1797 (1946); Angew. Chem. Int. Ed., 4, 300 (1965). These electrophilic alkenes readily undergo conjugate addition reactions with various nucleophiles:
Reaction with pentafluorophenol, in the presence of Et3N, gives PFP vinylsulfonate, which can be converted to a sulfonamide via tin-mediated radical addition of alkyl halides to the olefinic bond, followed by displacement of the PFP group with an amine: Org. Lett., 42549 (2002).
Hazard Statements: H301-H330-H314-H318
Toxic if swallowed. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P301+P310a-P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501a
IF SWALLOWED: Immediately call a POISON CENTER/doctor IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.