Triphenylphosphine_sulfide

Triphenylphosphine sulfide

Triphenylphosphine sulfide

Chemical compound

Triphenylphosphine sulfide (IUPAC name: triphenyl-λ5-phosphanethione) is the organophosphorus compound with the formula (C6H5)3PS, usually written Ph3PS (where Ph = phenyl). It is a colourless solid, which is soluble in a variety of organic solvents.

Quick Facts Names, Identifiers ...

Structurally, the molecule resembles the corresponding oxide, with idealized C3 point group symmetry.[1] It is weakly nucleophilic at the sulfur atom.

Applications

Organic synthesis

Triphenylphosphine sulfide is useful for the conversion of epoxides to the corresponding episulfides:[2]

Ph2C2H2O + Ph3PS → Ph2C2H2S + Ph3PO

It also reacts with ketenes to form thioketenes:[3]

Ph2CCO + Ph3PS → Ph2CCS + Ph3PO

Analytical chemistry

In analytical chemistry, triphenylphosphine is used for the analysis of certain kinds of sulfur compounds. Elemental sulfur (S8), as occurs in some oils, and labile organosulfur compounds, such as organic trisulfides, react with triphenylphosphine to give Ph3PS, which can be detected by gas chromatography.

References

  1. [1]
    Codding, P. W.; Kerr, K. A. (1978). "Triphenylphosphine sulfide". Acta Crystallographica Section B. 34 (12): 3785. Bibcode:1978AcCrB..34.3785C. doi:10.1107/S0567740878012212.
  2. [2]
    Mayhew, Darrin L.; Clive, Derrick L. J. (Apr 15, 2001). "Triphenylphosphine Sulfide". Encyclopedia of Reagents for Organic Synthesis. New York, NY: John Wiley. doi:10.1002/047084289X.rt379. ISBN 0-471-93623-5.
  3. [3]
    Staudinger, H.; Meyer, Jules (1919). "Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine". Helvetica Chimica Acta. 2 (1): 635–646. doi:10.1002/hlca.19190020164. ISSN 0018-019X.
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