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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container_title	Journal of organic chemistry
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description	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.
doi_str_mv	10.1021/jo801423a
format	Article
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subjects	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
title	Structural and Spatial Considerations in the N,N′-Diacyl- and Bis(alkoxycarbonyl)bispidinone Series
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