Benzisothiazoline-3-thione 1,1-Dioxides

2-Benzisothiazoline-3-thione 1,1-Dioxides. - The sodium salt of 1,2-benziso-thiazoline-3-thione 1,1-dioxide (67), when treated with RX (R = PhCH2, 

PhCH2CH2, PhCH=CHCH2, CH2=CHCH2, CH CCHj, NCCH2, orMe X = Cl, Br, or I) gives 80-93% of (68). From the latter, the corresponding thiols RSH are produced with piperidine in almost quantitative yield. Compound (68) is claimed as being an odourless crystalline equivalent of thiols. 

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Benzisothiazoline-3-thione 1,1-Dioxides 156 -Substitution of 1,2-Benzisothiazolin-3-ones 157... 

Synthesis of 1,2-Benzisothiazolin-3-ones (1,1-Dioxides) 156 From 2-(methylsulphinyl)benzamides or ]i-[2-(methylthio)benzoyl]- -alkylhydroxylamines and SOCI2 156 Physical Properties of 1,2-Benzisothiazolin-3-ones 156 Reactions of 1,2-Benzisothiazolin-3-ones 156 With activated methylene compounds 156 1,2-Benzisothiazoline-3-thione 1,1-Dioxides 156 N -Substitution of 1,2-Benzisothiazolin-3-ones 157... 

Benzisothiazole 2,2-dioxide is prepared by treating the 2-aminobenzoylsulfonic acid sodium salt with phosphorus oxychloride <86JHC1645>. The sodium dithiocarboxylate (230) on treatment with an acid or iodine gives the 2,1-benzisothiazoline 3-thione (231) <82JOC5255>. 

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