Reactions of N-sulfenyl-1,2-benzisothiazolin-3-ones with nucleophiles

Reactions of N-[2-(alkoxycarbonyl)benzenesulfenyl]-1,2-benzisothiazolin-3-ones () with various nucleophiles were examined. Anions of active methylene compounds attacked the sulfur atoms of the sulfenyl moieties of to afford sulfide compounds, while thiols attacked the sulfur atoms of the benzisothiazolinone moieties of to afford ring-opened products. Grignard reagents attacked both the above sulfur atoms to give ring-opened products along with sulfide compounds.