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A sterically congested cis-stilbene and its phosphonium salt precursor.

Shivanna Shivaprakash1, G Chandrasekara Reddy1, Jerry P Jasinski2

  • 1Chemical Sciences, Vittal Mallya Scientific Research Foundation (VMSRF), 94/3 and 94/5, 23rd Cross, 29th Main, BTM 2nd Stage, Bangalore 560 076, India.

Acta Crystallographica. Section C, Structural Chemistry
|June 6, 2015
PubMed
Summary

Triphenyl(2,4,5-trimethoxybenzyl)phosphonium chloride monohydrate was synthesized and used in Wittig reactions to create substituted stilbenes. The Z-configuration of hexamethoxystilbene was confirmed, revealing steric congestion and a nonplanar alkene fragment.

Keywords:
Wittig reactioncrystal structurehydrogen bondingphosphonium saltpolyalkoxy-substituted stilbenessteric congestion

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Spectroscopy

Background:

  • Synthesis of phosphonium salts is crucial for organic transformations.
  • Wittig reactions are widely used for alkene synthesis.
  • Understanding molecular geometry and intermolecular interactions is key in crystallography.

Purpose of the Study:

  • To synthesize triphenyl(2,4,5-trimethoxybenzyl)phosphonium chloride and its monohydrate.
  • To investigate the Wittig reaction of the phosphonium salt with alkoxy-substituted benzaldehydes.
  • To determine the structure and configuration of the resulting substituted stilbenes, particularly hexamethoxystilbene.

Main Methods:

  • Anhydrous reaction of triphenylphosphane and 2,4,5-trimethoxybenzyl chloride.
  • Crystallization of the phosphonium salt monohydrate.
  • Wittig reactions using potassium tert-butoxide as a base.
  • Nuclear Magnetic Resonance (NMR) spectroscopy for configuration assignment.
  • X-ray crystallography for structural analysis.

Main Results:

  • Formation of triphenyl(2,4,5-trimethoxybenzyl)phosphonium chloride and its stoichiometric monohydrate.
  • Synthesis of multiply substituted stilbenes, predominantly with Z-configuration.
  • Confirmation of the Z-configuration for (Z)-2,2',4,4',5,5'-hexamethoxystilbene.
  • Structural analysis revealed significant steric congestion and a nonplanar alkene fragment (torsion angle 7.8(4)°) in hexamethoxystilbene.
  • Crystal structure of the hydrated salt showed hydrogen bonding forming sheet structures, while hexamethoxystilbene exhibited no direction-specific intermolecular interactions.

Conclusions:

  • The Wittig reaction provides a versatile route to Z-stilbenes.
  • Steric hindrance significantly influences the planarity of the central double bond in highly substituted alkenes.
  • The crystal structures elucidate the role of hydrogen bonding in phosphonium salt hydrates and the packing of sterically demanding molecules.