Reduktone von Tetron-, Thiotetron- und Tetramsäuren, II. Reduktone durch Rhodium-katalysierte Zersetzung von Diazoverbindungen
✍ Scribed by Stachel, Hans-Dietrich ;Poschenrieder, Hermann ;Redlin, Jutta ;Schachtner, Josef ;Zeitler, Klaus
- Publisher
- John Wiley and Sons
- Year
- 1994
- Tongue
- English
- Weight
- 376 KB
- Volume
- 1994
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Reductones of Tetronic, Thiotetronic and Tetramic Acids, II. – Reductones by Rhodium‐Catalyzed Decomposition of Diazo Compounds
The diazoketones 2 have been synthesized by diazo transfer reaction with 2‐azido‐3‐ethylbenzthiazolium tetrafluoroborate. The rhodium‐catalyzed decomposition of compounds 2 in tert‐butyl alcohol at 130°C furnishes the reductone monoethers 3 and after deprotection the aci‐reductones 4. Methylation of compounds 4 with diazomethane proceeds stepwise leading first to the monoethers 5 and then to the diethers 6. The thiolactone 4b and even more the lactams 4c and 4d are stronger reducing agents than the lactone 4a. magnified image