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NMR spectroscopy of organophosphorus compounds II: Stereochemistry of [1-(2H-azirin-2-yl)alkyl]phosphonates

NMR-Spektroskopie von phosphororganischen Verbindungen, 2. Mitt.: Stereochemie von [1-(2H-Azirin-2-yl)alkyl]phosphonaten

  • Organische Chemie Und Biochemie
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Summary

The conformation and relative configuration of [1-(2H-azirin-2-yl)alkyl]phosphonates (2) has been established by thorough investigation of some characteristic representatives of the series by1H,13C,15N, and31P NMR spectroscopy. It is shown that the chemical shift of the proton located α to the phosphonate group can be used as a criterion for the discrimination and stereochemical assignment of diastereoisomers. NMR spectroscopic features of the compounds are discussed in terms of structural relationships.

Zusammenfassung

Die detaillierte NMR-spektroskopische Untersuchung (1H,13C,15N,31P) einiger charakteristischer Vertreter von [1-(2H-Azirin-2-yl)alkyl]phosphonaten erlaubte es, Konformation und relative Konfiguration der betreffenden Verbindungen zu bestimmen. Die chemische Verschiebung des bezüglich des Phosphonatrests α-ständigen Protons kann als Kriterium zur Unterscheidung und stereochemischen Zuordnung von Diastereomeren herangezogen werden. Die Phänomenologie der NMR-Spektren wird im Zusammenhang mit strukturellen Parametern diskutiert.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Vienna University, A-1090, Vienna, Austria

    H. Kalchhauser & E. Öhler

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  1. H. Kalchhauser
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  2. E. Öhler
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Dedicated to Univ.-Prof. Dr.K. Schlögl with the best wishes to his 70th birthday

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Kalchhauser, H., Öhler, E. NMR spectroscopy of organophosphorus compounds II: Stereochemistry of [1-(2H-azirin-2-yl)alkyl]phosphonates. Monatsh Chem 125, 1101–1111 (1994). https://doi.org/10.1007/BF00811518

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  • DOI: https://doi.org/10.1007/BF00811518

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