2-Hydroxyethanesulfonyl chloride

Figure 1. pH-Rate profile for hydrolysis of 2-hydroxyethanesulfonyl chloride (IX) in water at 25.0 °C, circles (O) refer to reaction in a medium maintained at ionic strength 0.3 M with NaCl04 squares (TD) refer to the reaction in 1 M NaCl (no NaCl04). 

Figure 3. Variation in the pseudo-first-order rate constant for the reaction of 2-hydroxyethanesulfonyl chloride (IX) with aqueous sodium chloride solution (pH 5.00 and ionic strength was 0.3 M with NaCl04, 25.0 °C).

Several j3-sultones are claimed to be formed by treatment of alkenes with sulfuric acid or by heating alkenesulfonic acids. Treatment of 2,2-dimethyl-1,1-diphenyl-1-propanol with concentrated sulfuric acid at room temperature is said to give 3-(l,l-diphenylethyl)-3-methyl-l,2-oxathietane 2,2-dioxide (96% yield). Treatment of sodium 3-bromo-2-hydroxybutanesulfonate with phosphorus trichloride is reported to give a low yield of 4-(l-bromoethyl)-l,2-oxathietane 2,2-dioxide.1,2-Oxathietane 2,2-dioxide is suggested as an intermediate in the reaction of /3-hydroxyethanesulfonyl chloride with trimethylamine to give the zwitterion 502. The first four-membered monocycUc sulfurane oxides 502a have been reported. 

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