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Diphospha-Ureas from the Phosphaketene Ph3 GePCO.

Kevin M Szkop1, Andrew R Jupp1, Hlib Razumkov1

  • 1Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario, M5S3H6, Canada.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 20, 2019
PubMed
Summary

Researchers developed a modular synthesis for diphospha-ureas using phosphaketene and phosphide precursors. This novel method allows for the creation of diverse unsymmetrical compounds with potential applications in materials science.

Keywords:
main-group elementsphospha-ureasphosphaethynolatesphosphaketenesphotochemistry

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Area of Science:

  • Organometallic Chemistry
  • Synthetic Chemistry
  • Phosphorus Chemistry

Background:

  • Diphospha-ureas are an important class of organophosphorus compounds.
  • Existing synthetic routes often lack modularity and versatility.
  • The development of new synthetic strategies is crucial for accessing novel diphospha-urea derivatives.

Purpose of the Study:

  • To establish the first modular synthesis for dissymmetric diphospha-ureas.
  • To explore the reactivity of novel diphospha-urea compounds.
  • To investigate the thermal and photochemical properties of synthesized species.

Main Methods:

  • Reaction of phosphaketene (Ph₃GePCO) with potassium phosphide (KP(tBu)₂).
  • Electrophilic trapping of the generated anion with methyl iodide (CH₃I) or chlorotriphenylgermane (ClGePh₃).
  • Sequential deprotonation and alkylation for further functionalization.
  • Analysis of thermal and photochemical reactivity.

Main Results:

  • Successful synthesis of dissymmetric diphospha-ureas via a modular approach.
  • Formation of novel compounds (tBu)₂PC(O)P(GePh₃)(CH₃) and (Ph₃Ge)₂PC(O)P(tBu)₂.
  • Demonstration of a route to symmetrical diphospha-ureas (tBu)₂PC(O)P(CH₃)₂.
  • Characterization of the thermal and photochemical behavior of the synthesized diphospha-ureas.

Conclusions:

  • A novel and modular synthetic strategy for diphospha-ureas has been developed.
  • This method provides access to a range of dissymmetric and symmetric diphospha-urea compounds.
  • The synthesized compounds exhibit interesting thermal and photochemical reactivity, opening avenues for further research.