Formation of thioacetals from sulfoxides under Pummerer-type conditions
β Scribed by Harris, Thomas D.; Boekelheide, V.
- Book ID
- 127291719
- Publisher
- American Chemical Society
- Year
- 1976
- Tongue
- English
- Weight
- 400 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
Trifluoroacetic anhydride induced Pummerer reactions of carbazole-sulfoxide 1 follow an unusual pathway, in which the initially formed acyloxysulfonium salt 3 undergoes not the usual abstract of m-proton but internal nucleophilic substitution with the indole nuclear followed by SN'type reaction of a
All attempts to convert compound (I) into (VI) fail. It is noteworthy that also DDQ reacts with (I) to give (III) in 37% yield. The structure of (III) is determined by X-ray analysis. Mechanistical aspects are discussed. -
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