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The first stable beta-fluorosilylanion.

Roland Fischer1, Judith Baumgartner, Guido Kickelbick

  • 1Institut für Anorganische Chemie, Technische Universität Graz, Austria.

Journal of the American Chemical Society
|March 20, 2003
PubMed
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Researchers synthesized a potassium adduct of 1-potassio-2-fluorotetrakis(trimethylsilyl)disilane. This intermediate readily forms tetrakis(trimethylsilyl)disilene, which can undergo cycloaddition or dimerization.

Area of Science:

  • Organosilicon Chemistry
  • Main Group Chemistry
  • Synthetic Inorganic Chemistry

Background:

  • Organosilicon compounds are versatile building blocks in synthesis.
  • Disilenes, silicon analogs of alkenes, are reactive intermediates.
  • Understanding the reactivity of polysilylated silicon compounds is crucial for developing new synthetic methodologies.

Purpose of the Study:

  • To investigate the reactivity of tris(trimethylsilyl)silyl fluoride.
  • To explore the formation and trapping of tetrakis(trimethylsilyl)disilene.
  • To characterize novel organosilicon adducts and their reaction pathways.

Main Methods:

  • Reaction of tris(trimethylsilyl)silyl fluoride with potassium tert-butoxide in the presence of donor ligands (THF, DME, 18-crown-6).

Related Experiment Videos

  • Isolation and characterization of the potassium adduct.
  • Attempted transmetalation reactions to generate tetrakis(trimethylsilyl)disilene.
  • Trapping experiments with cycloaddition reagents and observation of dimerization.

    • Main Results:

    • Clean formation of a potassium adduct of 1-potassio-2-fluorotetrakis(trimethylsilyl)disilane was achieved.
    • Transmetalation led to the elimination of potassium fluoride and the formation of tetrakis(trimethylsilyl)disilene.
    • Tetrakis(trimethylsilyl)disilene was successfully trapped via cycloaddition and observed to dimerize to octakis(trimethylsilyl)cyclotetrasilane in the absence of trapping agents.

    Conclusions:

    • The potassium adduct serves as a convenient precursor to tetrakis(trimethylsilyl)disilene.
    • The high reactivity of tetrakis(trimethylsilyl)disilene allows for facile cycloaddition and dimerization reactions.
    • This study provides insights into the synthetic utility of polysilylated silicon compounds and the generation of low-coordinate silicon species.