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Bis(trifluoroacetyl) peroxide, CF(3)C(O)OOC(O)CF(3).

R Kopitzky1, H Willner, A Hermann

  • 1Institut für Physikalische und Theoretische Chemie, Universität Tübingen, Auf der Morgenstelle 8, D-72076 Tübingen, Germany.

Inorganic Chemistry
|May 29, 2001
PubMed
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Highly explosive bis(trifluoromethyl) peroxide, CF(3)C(O)OOC(O)CF(3), was synthesized. This compound is a stable, clean source of trifluoromethyl radicals, CF(3), with potential applications in radical chemistry.

Area of Science:

  • Chemistry
  • Organic Chemistry
  • Physical Chemistry

Background:

  • Peroxides are known for their reactivity and use as radical initiators.
  • Trifluoromethyl radicals (CF(3)) are important in organic synthesis and materials science.
  • The synthesis and characterization of novel peroxide compounds are crucial for expanding chemical methodologies.

Purpose of the Study:

  • To synthesize and characterize pure bis(trifluoromethyl) peroxide, CF(3)C(O)OOC(O)CF(3), for the first time.
  • To investigate the stability and physical properties of CF(3)C(O)OOC(O)CF(3).
  • To explore the potential of CF(3)C(O)OOC(O)CF(3) as a source of CF(3) radicals.

Main Methods:

  • Low-temperature reaction of trifluoroacetyl chloride (CF(3)C(O)Cl) with sodium peroxide (Na(2)O(2)).

Related Experiment Videos

  • Characterization using NMR, vibrational, UV spectroscopy, gas electron diffraction, and quantum chemical calculations.
  • Vapor pressure measurements to determine boiling point and thermal stability analysis.

    • Main Results:

    • Pure, highly explosive CF(3)C(O)OOC(O)CF(3) was successfully synthesized.
    • The compound exhibits stability at room temperature in liquid and gaseous states, with a melting point of -37.5 °C and a boiling point of 44 °C.
    • Unimolecular decay above room temperature yields C(2)F(6) and CO(2) with an activation energy of 129 kJ mol(-1).
    • Matrix-isolation experiments confirmed CF(3)C(O)OOC(O)CF(3) as a clean source of CF(3) radicals.
    • Gas electron diffraction and quantum chemical calculations revealed a syn-syn conformation with a specific O-O bond length and dihedral angle.

    Conclusions:

    • Bis(trifluoromethyl) peroxide is a novel, synthetically accessible compound.
    • Its stability at room temperature and clean radical generation make it a promising reagent.
    • The detailed structural and thermal characterization provides a foundation for its future applications.