Triphenylphosphine sulfide

Triphenylphosphine sulfide
Names
IUPAC names
Triphenyl-λ5-phosphanethione
Triphenylphosphane sulfide
Triphenylphosphine sulfide
Preferred IUPAC name
Triphenyl-λ5-phosphanethione
Other names
Triphenylthioxophosphorane
Identifiers
3878-45-3 N
ChemSpider 18610 YesY
Jmol interactive 3D Image
PubChem 19758
Properties
C18H15PS
Molar mass 294.350461 g/mol
Appearance white solid
Melting point 161 to 163 °C (322 to 325 °F; 434 to 436 K)
dichloromethane, ethanol
Related compounds
Related compounds
Triphenylphosphine oxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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

Structurally, the molecule resemble the corresponding oxide, with ideallized C3v point group symmetry.[1] It is weakly nucleophilic at sulfur.

Applications

Organic synthesis

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

Ph2C2H2O + Ph3PS → Ph2C2H2S + 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, e.g. organic trisulfides, react with triphenylphosphine to give Ph3PS, which can be detected by gas chromatography.

References

  1. Codding, P. W.; Kerr, K. A. (1978). "Triphenylphosphine sulfide". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 34 (12): 3785. doi:10.1107/S0567740878012212.
  2. Darrin, L. Mayhew, Derrick L. J. Clive, "Triphenylphosphine Sulfide" in Encyclopedia of Reagents for Organic Synthesis, John Wiley, 2001, New York.doi:10.1002/047084289X.rt379 Article Online Posting Date: April 15, 2001
This article is issued from Wikipedia - version of the Monday, November 02, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.