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beta-Nitro xanthates as olefin precursors.

Gilles Ouvry1, Béatrice Quiclet-Sire, Samir Z Zard

  • 1Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, 91128 Palaiseau, France.

Organic Letters
|August 2, 2003
PubMed
Summary

Potassium O-ethyl xanthate reacts with nitroalkenes to form beta-nitro xanthates. These intermediates efficiently eliminate to produce olefins with high E selectivity using mild heating and lauroyl peroxide.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Reaction Mechanisms

Background:

  • Olefins are crucial building blocks in organic synthesis.
  • Developing efficient and selective methods for olefin synthesis is an ongoing challenge.
  • Xanthate chemistry offers unique pathways for functional group transformations.

Purpose of the Study:

  • To investigate the reaction of potassium O-ethyl xanthate with alpha,beta-unsaturated nitro compounds.
  • To develop a novel tin-free elimination method for generating olefins.
  • To achieve high yields and stereoselectivity in olefin formation.

Main Methods:

  • Addition reaction of potassium O-ethyl xanthate to various alpha,beta-unsaturated nitro compounds.
  • Thermal elimination of the resulting beta-nitro xanthates using lauroyl peroxide in refluxing 1,2-dichloroethane.
  • Analysis of products for yield and E/Z selectivity using spectroscopic methods.

Main Results:

  • Stable beta-nitro xanthate intermediates were successfully synthesized.
  • Tin-free elimination proceeded smoothly upon heating with lauroyl peroxide.
  • Olefins were obtained in good yields with high E selectivity.

Conclusions:

  • A new synthetic route to olefins from nitroalkenes via beta-nitro xanthates has been established.
  • The developed method provides a mild, efficient, and stereoselective approach to olefin synthesis.
  • This methodology avoids the use of toxic organotin reagents.

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