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The alpha-iminophospholide ligands.

Joanna Grundy1, Bruno Donnadieu, François Mathey

  • 1UCR-CNRS Joint Research Chemistry Laboratory, Department of Chemistry, University of California Riverside, Riverside, California 92521-0403, USA.

Journal of the American Chemical Society
|June 15, 2006
PubMed
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Researchers synthesized novel alpha-iminophospholide ligands from phospholide ions and imidoyl chlorides. These ligands form complexes with metal chlorides, featuring significant electronic delocalization and unique structural properties.

Area of Science:

  • Organometallic Chemistry
  • Phosphorus Chemistry
  • Coordination Chemistry

Background:

  • Phospholide ions are versatile nucleophiles in organophosphorus chemistry.
  • Imidoyl chlorides serve as electrophilic partners for forming carbon-nitrogen bonds.

Purpose of the Study:

  • To synthesize novel alpha-iminophospholide ligands.
  • To explore the coordination chemistry of these ligands with metal chlorides.
  • To investigate the electronic and structural properties of the resulting complexes.

Main Methods:

  • Reaction of phospholide ions with imidoyl chlorides in the presence of potassium tert-butoxide (tBuOK).
  • Isolation of trimethylstannyl derivatives of alpha-iminophospholides.
  • Complexation reactions with various metal chlorides.

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  • Density Functional Theory (DFT) calculations.
  • X-ray crystallography.

    • Main Results:

    • Successful synthesis of alpha-iminophospholides and their trimethylstannyl derivatives.
    • Formation of metal complexes with the title ligands.
    • DFT studies revealed significant electronic delocalization between the imino group and the phospholyl ring.
    • X-ray structure of a stannylphosphole showed a highly pyramidal phosphorus atom.
    • A tetrameric copper complex was structurally characterized.

    Conclusions:

    • Alpha-iminophospholides are accessible ligands for coordination chemistry.
    • The electronic structure of these ligands exhibits significant pi-delocalization.
    • The unique structural features, including pyramidal phosphorus, are important for complex formation.