Triphenylphosphine sulfide

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Triphenylphosphine sulfide
Triphenylphosphine-sulfide-2D-skeletal.png
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Names
IUPAC names
Triphenyl-λ5-phosphanethione
Triphenylphosphane sulfide
Triphenylphosphine sulfide
Preferred IUPAC name
Triphenyl-λ5-phosphanethione
Other names
Triphenylthioxophosphorane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.021.280
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).
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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[edit]

Organic synthesis[edit]

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

Ph2C2H2O + Ph3PS → Ph2C2H2S + Ph3PO

Analytical chemistry[edit]

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[edit]

  1. ^ Codding, P. W.; Kerr, K. A. (1978). "Triphenylphosphine sulfide". Acta Crystallographica Section B. 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