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Related Experiment Videos

Cyclic (1R,3R)-1,3-dimethyltrimethylene [(5R)-2-hydroxy-5-methyl-5-(2-

M A Capron1, J An, D C Swenson

  • 1Department of Chemistry, University of Iowa, Iowa City 52242, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|March 15, 1995
PubMed
Summary

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A novel beta-keto phosphonate compound, C16H27O6P, rearranges from vinyl phosphate. In solution, it forms three isomers, but crystallizes as a single R-stereochemistry enol form.

Area of Science:

  • Organic Chemistry
  • Organophosphorus Chemistry
  • Stereochemistry

Background:

  • Vinyl phosphates are precursors to organophosphorus compounds.
  • Isomerization and tautomerization are common phenomena in organic molecules.
  • Beta-keto phosphonates exhibit diverse chemical properties.

Purpose of the Study:

  • To characterize the C16H27O6P compound obtained from vinyl phosphate rearrangement.
  • To investigate the solution and crystalline state behavior of the title compound.
  • To determine the stereochemistry of the crystalline isomer.

Main Methods:

  • Chemical synthesis via vinyl phosphate rearrangement.
  • Solution-state Nuclear Magnetic Resonance (NMR) spectroscopy, specifically 31P NMR.

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  • X-ray diffraction analysis for crystalline structure determination.

    • Main Results:

    • The title compound, C16H27O6P, was successfully synthesized.
    • 31P NMR revealed an equilibrium mixture of three isomers in solution.
    • X-ray diffraction identified the crystalline form as the enol tautomer with R stereochemistry at C(8).

    Conclusions:

    • The compound exists as a mixture of isomers in solution but adopts a specific enol form in the solid state.
    • Stereochemical assignment of the crystalline isomer provides crucial structural information.
    • Understanding the isomerization and tautomerization is key to its chemical applications.