✦ LIBER ✦
ChemInform Abstract: A Simple Entry to Fused N-Aryl 1,2-Thiazetidine-S-oxides: Thermal Isomerization to 1,4-Thiazine-S-oxides and Nucleophilic Ring-Opening with Alcohols and Amines.
✍ Scribed by R. N. WARRENER; A. S. AMARASEKARA
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 31 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Thermal Isomerization to 1,4-Thiazine-S-oxides and Nucleophilic Ring-Opening with Alcohols and Amines.
-Thiazetidines (III), readily produced by cycloaddition of quadricyclane with aryl sulfonylamines undergo smooth thermal rearrangement to thiazines like (IV) with S-oxide configuration that differs with the type of the aryl group. No thiazetidine intermediate is observed in the reaction of quadricyclane (I) with sulfonylamine (V) . A stereoselective access to norbornene sulfinates and sulfinamides, e.g. (VIII) and (X), is the ring opening of (III) with alcohols and amines.