Reactions of benzyl aryl sulfides with excess active halogen reagents
1,2,3-Tribromopyrrolo[1,2-b][1,2]benzothiazin-10-one (2) is produced from 2-[2-(benzylthio)benzoyl]-pyrrole (1) when treated with excess (5 equiv) NBS in CHCl3. With NCS, a mixture is obtained in which di- and trichloropyrrolo[1,2-b][1,2]benzothiazin-10-ones are present. If ethanol is present in the NCS reaction, compound 4 is formed as the major product. Further, compound 3 is also formed by the reaction of compound 1 or the corresponding disulfide with excess SOCl2. A novel route to alkyl arenesulfinic esters is also reported. Treatment of a benzyl aryl sulfide with excess (5 equiv) NCS in the presence of an n-alkyl alcohol (7 equiv) produces an n-alkyl arenesulfinic ester in good yield. An arenesulfonyl chloride is the major product in the presence of benzyl alcohol.
Journal of Organic Chemistry
Reactions of benzyl aryl sulfides with excess active halogen reagents.
Journal of Organic Chemistry,
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