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Atropisomerism of 1-alkylcyclohepta [b]pyrrol-2(1H)-ones. Isolation of the rotational isomers of 1-(2,4-dimethyl-3-pentyl)cyclohepta [b]pyrrol-2(1H)-one

✍ Scribed by Yukari Ikeda; Nobuo Kato; Akira Mori; Hitoshi Takeshita

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
474 KB
Volume
30
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

1‐Alkylcyclohepta[b]pyrrol‐2(1__H__)‐ones showed rotational isomerism around the CN bond. Two rotamers of the 1‐(2,4‐dimethyl‐3‐pentyl) derivative were isolable by high‐performance liquid chromatography at 0°C. The activation free energy, measured by the line‐shape analysis of the variable‐temperature NMR spectra, was 86.8 kJ mol^−1^ at 25°C. In a bromo derivative, a positive buttressing effect was observed.

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