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Related Experiment Videos

Phosphepines: convenient access to phosphinidene complexes.

Mark L G Borst1, Rosa E Bulo, Christiaan W Winkel

  • 1Department of Organic Chemistry, Faculty of Sciences, Vrije Universiteit, De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands.

Journal of the American Chemical Society
|April 21, 2005
PubMed
Summary
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Primary phosphines react with o-diethynylbenzene to form stable phosphepine complexes. These complexes decompose to phosphinidene complexes, which can be trapped by various unsaturated compounds.

Area of Science:

  • Organometallic Chemistry
  • Phosphorus Chemistry

Background:

  • Transition metal-complexed primary phosphines are versatile reagents.
  • Phosphepine complexes are known intermediates in phosphorus chemistry.

Purpose of the Study:

  • To investigate the reaction of o-diethynylbenzene with transition metal-complexed primary phosphines.
  • To characterize the resulting phosphepine complexes and their subsequent decomposition products.

Main Methods:

  • Base-induced cyclization reaction.
  • X-ray crystallography for structural confirmation.
  • Trapping experiments with alkenes, alkynes, and alcohols.

Main Results:

  • Stable phosphepine complexes were synthesized in a single step.

Related Experiment Videos

  • Phosphepines underwent cheletropic elimination of naphthalene at elevated temperatures.
  • Transient phosphinidene complexes were generated and trapped in high yields.

    • Conclusions:

    • A novel route to stable phosphepine complexes was established.
    • The facile generation and trapping of phosphinidene complexes from phosphepines is demonstrated.
    • This methodology offers a new pathway for synthesizing organophosphorus compounds.