Thioanisole Explained

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.

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.^[1]

Oxidation of sulfur via addition of a single oxygen atom gives methyl phenyl sulfoxide,^[2] a reaction useful for titration of oxidants such as dimethyldioxirane.^[3] Successive oxidation then leads to the sulfone.

References

1. Bailey, Simon "Thioanisole" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons.
2. Org. Syntheses. Carl R. . Johnson . Jeffrey E. . Keiser . Methyl Phenyl Sulfoxide . 1966 . 46 . 78 . 10.15227/orgsyn.046.0078.
3. Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations . Waldemar . Adam . Yuk Yee . Chan . Dieter . Cremer . Juergen . Gauss . Dieter . Scheutzow . Michael . Schindler . J. Org. Chem. . 1987 . 52 . 13 . 2800–2803 . 10.1021/jo00389a029 .