Stereospezifische 1,2-Wanderungen von Hydroxyl-, Aryl- und Alkyl- gruppen bei der Nitrosierung von Aminosäuren in Fluorwasserstoff/Pyridin. Vorläufige mitteilung
✍ Scribed by Rolf Keck; János Rétey
- Publisher
- John Wiley and Sons
- Year
- 1980
- Tongue
- German
- Weight
- 199 KB
- Volume
- 63
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
Stereospecific 1,2‐Migration of Hydroxyl, Aryl and Alkyl Groups during the Nitrosation of Amino Acids in Hydrogenfluoride/Pyridine Vorläufige Mitteilung
The nitrosation of α‐amino acids in hydrogenfluoride/pyridine was reinvestigated. In contrast to recent reports [1] [2] it was found that this reaction takes place either with entire (phenylalanine, tyrosine, threonine) or partial (valine, isoleucine) rearrangement to yield β‐fluorocarboxylic acids. Glycine, alanine and α‐aminobutanoic acid were converted exclusively into the α‐fluorocarboxylic acids. The substitution of the amino group takes place with stereochemical retention as revealed by NMR. examination of the 2‐fluoro‐3‐methylpentanoic acids obtained from L‐isoleucine and D‐alloisoleucine, respectively.