Structural and spatial considerations in the N,N′-diacyl- and bis(alkoxycarbonyl)bispidinone series

Shlomo Levinger; Yifat Sharabi-Ronen; Alexander Mainfeld; Amnon Albeck

doi:10.1021/jo801423a

Structural and spatial considerations in the N,N′-diacyl- and bis(alkoxycarbonyl)bispidinone series

Shlomo Levinger, Yifat Sharabi-Ronen, Alexander Mainfeld, Amnon Albeck

Research output: Contribution to journal › Article › peer-review

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Abstract

(Chemical Equation Presented) 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.

Original language	English
Pages (from-to)	7793-7796
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	73
Issue number	19
DOIs	https://doi.org/10.1021/jo801423a
State	Published - 3 Oct 2008

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10.1021/jo801423a

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AU - Mainfeld, Alexander

AU - Albeck, Amnon

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AB - (Chemical Equation Presented) 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.

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Structural and spatial considerations in the N,N′-diacyl- and bis(alkoxycarbonyl)bispidinone series

Abstract

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