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The tetra(vinyl)phosphonium cation [(CH2=CH)4P]+.

Uwe V Monkowius1, Stefan D Nogai, Hubert Schmidbaur

  • 1Anorganisch-chemisches Institut, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany.

Journal of the American Chemical Society
|February 12, 2004
PubMed
Summary

A new synthesis method for tetra(vinyl)phosphonium salts offers high yields. This research details the synthesis and structural characterization of these novel vinyl phosphonium compounds.

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Area of Science:

  • Organic Chemistry
  • Organophosphorus Chemistry
  • Materials Science

Background:

  • Tetra(vinyl)phosphonium salts are versatile building blocks.
  • Efficient synthesis routes for these compounds are limited.
  • Understanding their structural properties is crucial for applications.

Purpose of the Study:

  • To develop a convenient and high-yield synthesis for tetra(vinyl)phosphonium salts.
  • To characterize the synthesized compounds and their intermediates.
  • To investigate the ground-state conformation of the tetra(vinyl)phosphonium cation.

Main Methods:

  • Hydrophosphination of phosphine (PH3) with vinyl acetate.
  • Quaternization using 2-iodoethanol followed by acetylation.
  • Elimination of acetic acid to yield the final phosphonium salts.

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  • Characterization using analytical and spectroscopic data, including X-ray crystallography.
  • Quantum chemical calculations for conformational analysis.

    • Main Results:

    • A high-yield synthesis of tetra(vinyl)phosphonium salts was achieved.
    • The crystal structure of [Vi4P]+[BPh4]- revealed a low-symmetry (C1) propeller conformation for the cation.
    • This propeller conformation was found to be general for tetravinylelement species.
    • A contrast was drawn with the S4 symmetry typically observed in tetra(ethyl)element analogues.
    • Alkyltrivinylphosphonium salts were also synthesized using a similar procedure.

    Conclusions:

    • The developed synthetic route provides efficient access to tetra(vinyl)phosphonium salts.
    • The study elucidates the characteristic low-symmetry propeller conformation of tetravinylelement species.
    • This work contributes to the understanding and synthesis of organophosphorus compounds with potential applications.