Benzenesulfinyl chloride

As an alternative, Harpp and coworkers reacted benzenesulfinyl chloride with the trimethylsilyl derivative of menthol to form the diastereomeric esters in 91% yield the epimer of configuration R could be isolated by crystallization in unspecified yield. Grossert and coworkers prepared ester 19 in 51% yield as a mixture of diastereomers by treating p-toluenesulfonyl chloride with sodium p-toluenesulfinate in DMF containing menthol. It was postulated that initial nucleophilic attack by the sulfinate oxygen on the sulfonyl sulfur atom gave the mixed sulfonate-sulfinate anhydride 21, which then reacted... 

Acetyl bromide, 0728 f Acetyl chloride, 0735 f Aciyloyl chloride, 1093 Azidocarbonyl fluoride, 0339 Benzenesulfinyl chloride, 2234 Benzenesulfonyl chloride, 2235 Benzoyl chloride, 2675 Benzyl chloroformate, 2931... 

Jacobus and Mislow (85) reported that racemic benzenesulfinyl chloride reacts with chiral jV-methyl-2-phenylpropylamine to yield a mixture of the corresponding diastereomeric sulfinamides 76 that can be separated into pure components by fractional crystallization. 

Methyl benzenesulfinate has been prepared by the three-stage process of reduction of benzenesulfonyl chloride to benzenesulfinic add, conversion of the acid to benzenesulfinyl chloride, and esterification of the chloride with methanol. 7 It has been prepared also by ozonolysis of methyl benzenesulfenate.4 The present procedure is based on one reported by Field, Hoelzel, and Locke.6... 

Benzenesulfinyl azide, 2266 Benzenesulfinyl chloride, 2227 Benzenesulfonic anhydride, 3492 Benzenesulfonyl azide, 2267 Benzenesulfonyl chloride, 2228... 

Acetyl bromide, 0724 f Acetyl chloride, 0731 f Acryloyl chloride, 1090 Azidocarbonyl fluoride, 0338 Benzenesulfinyl chloride, 2227 Benzenesulfonyl chloride, 2228 Benzoyl chloride, 2671... 

Benzenesulfinamides 716 717 Benzenesulfinyl chloride is dissolved in five times the amount of ether and treated with 2 moles of amine at 0°. The precipitate is collected, washed with water, dissolved in ethanol, and reprecipitated by addition of a little water. Thus were obtained benzenesulfinamide, m.p. 121°, and its jV,jV-dimethyl derivative (readily soluble in ether), b.p. 90°/2-3 mm, benzenesulfinanilide, m.p. 112-114°, and l-(benzenesulfinyl)piperidine, m.p. 83°. 

Jacobus and Mislow have investigated the development of chiral sulfinamides as precursors to optically pure sulfoxides [22]. The reaction of benzenesulfinyl chloride and (5)-(+)-deoxyephedrine proceeded at low temperature (0°C) to yield... 

S-Labeled compounds. Chlorine bubbled slowly at 0° into a soln. of thio-phenol and acetic acid in dry methylene chloride until the orange color has faded to a pale yellow after ca. 1 hr., the solvent removed in K acuo, the resulting crude benzenesulfinyl chloride (Y 99-100% when isolated) dissolved in dry ether, thiophenol- S and pyridine in dry ether added slowly with stirring at —20° phenyl benzene- S-thiolsulfinate. Y 86%.—Phenyl benzene-thiol- S-sulfinate is prepared in identical manner with thiophenol- S used to make the benzenesulfinyl chloride. D. Barnard and E. J. Percy, Soc. 1962, 1667. 

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