A sigmatropic rearrangement involving dimethyl sulfoxide during an oxidation of a carbohydrate derivative
β Scribed by Nagarajan, Srinivasan; Rinehart, Kenneth L.
- Book ID
- 121278463
- Publisher
- American Chemical Society
- Year
- 1985
- Tongue
- English
- Weight
- 979 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
We wish to report the formation of the methylthiomethoxy derivative IV during attempted oxidation of 3S-hydroxyandrost-5-en-l7-one(I) with dimethylsulfoxide (DMSO) and dicyclohexylcarbodiimide (DCC). Compound IV presumably arises by rearrangement of the intermediate sulfoniumoxy salt III. (Dimethyls
## Abstract When reacted with potassium amide in liquid ammonia both 3βbromoβand 4βbromoβ1,5βnaphthyridine are converted into a mixture containing 3βaminoβ and 4βaminoβ1,5βnaphthyridine. The course of these reactions can be explained by a mechanism involving 1,5βnaphthyridyneβ3,4 as an intermediate