Relative Configuration and Conformation of 5-(Dimethoxyphosphoryl)-2-methoxy-1,2λ5-oxaphospholan-2-ones by Multinuclear NMR Spectroscopy |
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Authors: | Hermann Kalchhauser,Elisabeth
hler |
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Affiliation: | Hermann Kalchhauser,Elisabeth Öhler |
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Abstract: | Information on the hitherto unknown relative configuration and on the conformation of the title compounds in solution can be derived from nuclear Overhauser effects and coupling constants. Whereas the bridged 5-(dimethoxyphosphoryl)-2-methoxy-1,2λ5-oxaphospholan-2-ones 6 and 7 are sterically strained and, therefore, conformationally rigid, the C(3)-unsubstituted compound 1 does not show a preferred solution conformation. Phenyl substituents at C(3) (compounds 2 – 5 ) tend to adopt a pseudoequatorial position, this way leading to a definite conformation of the respective compounds. The influence of the conformation on the NMR spectra is discussed. 31P-NMR Spectroscopy is ideally suited for the characterization and quantification of the isomers 2 – 5 present in the reaction mixture. |
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