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Mechanism of sulfoxide-ketenimine and sulfoxide-carbodiimide oxidations

โœ Scribed by Robert E. Harmon; Carmen V. Zenarosa; S.K. Gupta

Book ID
104239838
Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
218 KB
Volume
10
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

In a recent c ommunication we have described the usefulness of sulfoxide-ketenimine in the oxidation of 2:Jb_-isopropylideneadenosine.1 We have now extended this new procedure to the oxidation of hydroxy.steroids. This is exemplified by the oxidation of testosterone to androst-4-ene-3,17-dione. With the help of hexadeuteriodimethylsulfoxide we have investigated the mechanism of sulfoxide-ketenimine and sulfoxide-carbodiimide.oxidations.2

Our proposed mechanism for the sulfoxide-ketenimine oxidation is outlined in Scheme I. Scheme I.

a.

๐Ÿ“œ SIMILAR VOLUMES

A pummerer type rearrangement during att
A pummerer type rearrangement during attempted oxidation with dimethyl sulfoxide and dicyclohexyl carbodiimide
โœ J. Bryan Jones; Donald C. Wigfield ๐Ÿ“‚ Article ๐Ÿ“… 1965 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 222 KB

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