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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
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Using the phospha-Michael reaction for making phosphonium phenolate zwitterions.

Matthias R Steiner1,2, Max Schmallegger3, Larissa Donner1,2

  • 1Institute for Chemistry and Technology of Materials, Graz University of Technology, Stremayrgasse 9, 8010 Graz, Austria.

Beilstein Journal of Organic Chemistry
|January 17, 2024
PubMed
Summary

Researchers synthesized nine novel phosphonium phenolate zwitterions via reactions with Michael acceptors. These compounds exhibit unique electronic properties and their formation kinetics reveal the rate-determining proton transfer step.

Keywords:
Lewis-base catalysisMichael acceptor reactivityphospha-Michael reactionphosphonium phenolate zwitterion

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Area of Science:

  • Organophosphorus Chemistry
  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Phosphonium salts and phenolates are versatile chemical entities.
  • Michael acceptors are crucial in organic synthesis for carbon-carbon bond formation.
  • Understanding zwitterion formation mechanisms is key to designing new molecules.

Purpose of the Study:

  • To synthesize and characterize novel phosphonium phenolate zwitterions.
  • To investigate the structural and electronic properties of these zwitterions.
  • To elucidate the kinetics and mechanism of their formation.

Main Methods:

  • Reaction of 2,4-di-tert-butyl-6-(diphenylphosphino)phenol with various Michael acceptors.
  • Synthesis and full characterization of nine zwitterions.
  • Single-crystal X-ray crystallography for solid-state structure determination.
  • Nuclear Magnetic Resonance (NMR) spectroscopy.
  • UV-vis spectroscopy.
  • Kinetic studies in different solvents (chloroform and methanol).

Main Results:

  • Nine phosphonium phenolate zwitterions were successfully synthesized and characterized.
  • Solid-state structures revealed significant ylidic resonance contribution.
  • Zwitterions show UV-vis absorptions around 360 nm with negative solvatochromism.
  • Kinetic analysis identified proton transfer as the rate-determining step.
  • Reactivity is influenced by Michael acceptor structure and solvent polarity.

Conclusions:

  • The study successfully synthesized and characterized novel phosphonium phenolate zwitterions.
  • Ylidic resonance plays a crucial role in the electronic structure of these molecules.
  • The formation mechanism is dependent on the Michael acceptor's ability to undergo preorganization and the solvent's properties.