A pummerer type rearrangement during attempted oxidation with dimethyl sulfoxide and dicyclohexyl carbodiimide
✍ Scribed by J. Bryan Jones; Donald C. Wigfield
- Publisher
- Elsevier Science
- Year
- 1965
- Tongue
- French
- Weight
- 222 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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. (Dimethylsulfoniumoxy salts of this type have been postulated as intermediates in oxidations involving DMSO (1,2),) This rearrangement, where C to 0 migration is + accompanied by rupture of the S-O bond, resembles the Pummerer reaction (3) in which sulfoxides react with acetic anhydride to give a-acetoxysulfides. However, as the latter