✦ LIBER ✦
Steroids and Sex Hormons. Part 263. [1]. On the Mechanism of the Reaction of 17-Hydroxyimino-steroids with Carbodiimide/Dimethylsulfoxide
✍ Scribed by Johannes Pfenninger; Walter Graf
- Publisher
- John Wiley and Sons
- Year
- 1980
- Tongue
- German
- Weight
- 183 KB
- Volume
- 63
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Treatment of the (Z)‐isomers 6 and 7 of the four isomeric 16‐acetoxy‐17‐hydroxyimino‐steroids 6–9 with DCC/DMSO/CF~3~COOH (Moffat fragmentation of oximes) yielded the seco‐α‐acetoxy‐nitriles 10 and 11, respectively, while similar treatment of both (E)‐isomers 8 and 9 gave the formyl‐carbonitrile 14. The mechanism of these fragmentations is discussed. ^13^C‐NMR. data of oximes are presented which show the γ‐gauche effect being associated with σ (CH)‐bond polarization.