Oxidation of Acceptor-substituted Isothiazolium-2-imines to Stable Cyclic Sulfin- and Sulfonamides with 3-Hydroperoxy Function
✍ Scribed by Arne Kolberg; Sabine Kirrbach; Dagmar Selke; Bärbel Schulze; Svetlana Morozkina
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 61 KB
- Volume
- 342
- Category
- Article
- ISSN
- 1615-4150
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✦ Synopsis
The oxidation of isothiazolium 2-imines 3,5 and their salts 4 to stable 3-hydroperoxy-2,3,4,5,6,7-hexahydro-1,2-benzisothiazole 1-oxides 7 and 1,1-dioxides 8 and 9 as a rac-cis-sultims 7c -e, g -i in moderate yields (13 -32%) after one hour as firstly isolatable products. Ring enlargement products like 1,2,3-thiadiazines 1, which were obtained by the oxidation of N-benzenesulfonyl-isothiazolium-2-imines [5], could not be observed. new class of cyclic sultims and sultams is described. The formation of 3-hydroxysultams 10 and isothiazol-3(2H)one 1,1dioxides 11 is presented.