Structural and Spatial Considerations in the N,N′-Diacyl- and Bis(alkoxycarbonyl)bispidinone Series

Structural and Spatial Considerations in the N,N′-Diacyl- and Bis(alkoxycarbonyl)bispidinone Series

Diamidic and dicarbamic bispidinones show trans−cis isomerism, the relative population in solution of the cis form increasing with solvent polarity. The mutual proximity of the two amide functions in 4a has no impact on the barrier to isomerization. The system represents a peculiar case of planar ch...

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Veröffentlicht in:Journal of organic chemistry 2008-10, Vol.73 (19), p.7793-7796
Hauptverfasser: Levinger, Shlomo, Sharabi-Ronen, Yifat, Mainfeld, Alexander, Albeck, Amnon
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Carbamates - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
Pyrones - chemistry
Solvents
Stereoisomerism
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Beschreibung
Zusammenfassung:Diamidic and dicarbamic bispidinones show trans−cis isomerism, the relative population in solution of the cis form increasing with solvent polarity. The mutual proximity of the two amide functions in 4a has no impact on the barrier to isomerization. The system represents a peculiar case of planar chirality posing a challenge to its specification.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801423a