✦ LIBER ✦
Regio- and stereoselective alkylation of a pyrrolidinic system: Structural and conformational studies by high field NMR techniques
✍ Scribed by M. Schaefer; P. Faller; D. Nicole
- Publisher
- John Wiley and Sons
- Year
- 1982
- Tongue
- English
- Weight
- 296 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
Abstract
A new merocyanine was prepared by addition of the pyrrolidine enamine of N‐ethoxycarbonylpyrrolidine‐3‐one to 1‐octyne‐3‐one. This addition was regioselective (with an unexpected C‐4 alkylation of the pyrrolidinone‐3‐enamine) and stereospecific (exclusively trans addition to the triple bond). The structure and conformational equilibrium were studied by high resolution proton magnetic resonance (NOE and variable temperature effects). Activation parameters Δ__H__*, Δ__S__* and Δ__G__* are given, and the behaviour on protonation examined.