Isomer Distribution of Succinylcyclohexenyl, Acetylcyclohexenyl and Acetylcyclopentenyl Enamines

A.   Gilbert   Cook; Sarah   L.   Folk

doi:10.2174/157017808784049452

Abstract

The isomeric distributions of some cyclohexenyl enamines substituted by succinyl or acetyl groups at either the 2- or 6-positions are reported as are the isomeric distributions of similarly substituted cyclopentenyl enamines. Correlation between the 13C NMR chemical shifts in these enamines and isomer distribution is shown. Density functional molecular modeling is used to demonstrate resonance and electrostatic effects on isomeric distributions.

Keywords: Cyclopentyl Enaminoketones, NMR, steric interactions, upfield chemical shifts, resonance

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Letters in Organic Chemistry

Title: Isomer Distribution of Succinylcyclohexenyl, Acetylcyclohexenyl and Acetylcyclopentenyl Enamines

Volume: 5 Issue: 4

Author(s): A. Gilbert Cook and Sarah L. Folk

Affiliation:

Keywords: Cyclopentyl Enaminoketones, NMR, steric interactions, upfield chemical shifts, resonance

Abstract: The isomeric distributions of some cyclohexenyl enamines substituted by succinyl or acetyl groups at either the 2- or 6-positions are reported as are the isomeric distributions of similarly substituted cyclopentenyl enamines. Correlation between the 13C NMR chemical shifts in these enamines and isomer distribution is shown. Density functional molecular modeling is used to demonstrate resonance and electrostatic effects on isomeric distributions.

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Cook Gilbert A. and Folk L. Sarah, Isomer Distribution of Succinylcyclohexenyl, Acetylcyclohexenyl and Acetylcyclopentenyl Enamines, Letters in Organic Chemistry 2008; 5 (4) . https://dx.doi.org/10.2174/157017808784049452