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Application of 1H/13C inversely correlated NMR spectroscopy to the determination of the stereochemistry of a polysubstituted [2.2]paracyclophane

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Fischer,  Rüdiger E.
Max Planck Institute for Medical Research, Max Planck Society;

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Dabrowski,  Janusz
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Ejchart,  Andrzej
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Staab,  Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Fischer, R. E., Dabrowski, J., Ejchart, A., & Staab, H. A. (1988). Application of 1H/13C inversely correlated NMR spectroscopy to the determination of the stereochemistry of a polysubstituted [2.2]paracyclophane. Magnetic Resonance in Chemistry, 26(10), 834-838. doi:10.1002/mrc.1260261006.


Cite as: http://hdl.handle.net/21.11116/0000-000A-5565-5
Abstract
The relative orientation of substituents in the opposite rings of one of the isomeric 4,7-Dichloro-5,8,12,15-tetramethoxy-13,6-bis[4-(2-methoxycarbonylphenyl) butyl][2.2]paracyclophanes was determined by establishing by NOE their orientation relative to the bridge protons, which thus served as ‘space-spy nuclei’. The mutual orientation of these bridge protons was ascertained by the analysis of their coupling constants, obtained from a phasesensitive COSY spectrum. The 1H and 13C resonances were assigned with the aid of 1H COSY and 1H/13C inversely correlated spectra.