Thioanisole

Thioanisole

Thioanisole

Chemical compound

Thioanisole is an organic compound with the formula CH3SC6H5. It is a colorless liquid that is soluble in organic solvents. It is the simplest alkyl–aryl thioether. The name indicates that this compound is the sulfur analogue—the thioether rather than the oxygen-centered ether—of anisole.

Quick Facts Names, Identifiers ...

It can be prepared by methylation of thiophenol.

Reactions

Alkyllithium reagents deprotonate thioanisole at the methyl group to afford C6H5SCH2Li, a strong nucleophile that can be alkylated to form more complex chains and structures. The resulting homologated thioether can be manipulated in a variety of ways.[2]

Oxidation of sulfur via addition of a single oxygen atom gives methyl phenyl sulfoxide,[3] a reaction useful for titration of oxidants such as dimethyldioxirane.[4] Successive oxidation then leads to the sulfone.

References

  1. [1]
    Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 707. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  2. [2]
    Bailey, Simon "Thioanisole" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons. doi:10.1002/047084289X.rt093
  3. [3]
    Johnson, Carl R.; Keiser, Jeffrey E. (1966). "Methyl Phenyl Sulfoxide". Org. Syntheses. 46: 78. doi:10.15227/orgsyn.046.0078.
  4. [4]
    Adam, Waldemar; Chan, Yuk Yee; Cremer, Dieter; Gauss, Juergen; Scheutzow, Dieter; Schindler, Michael (1987). "Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations". J. Org. Chem. 52 (13): 2800–2803. doi:10.1021/jo00389a029.
Share this article:

This article uses material from the Wikipedia article Thioanisole, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.