Thioether
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A thioether (also known as a sulfide) is a functional group in organic chemistry that has the structure C-S-C. A thioether is similar to an ether except that it contains a sulfur atom in place of the oxygen. Because the chemical properties of both atoms are similar, as they are in the same group in the periodic table, the chemical properties of ethers and thioethers share some commonalities. This functional group is important in biology, most notably in the amino acid methionine. Like many other sulfur containing compounds, volatile thioethers characteristically have foul odors.<ref>R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0 471 95512 4.</ref>
One difference from ethers is that ethers (R-O-R) are not readily oxidized, whereas thioethers (R-S-R) to sulfoxides (R-S(=O)-R), which can themselves be oxidized to sulfones (R-S(=O)2-R). For example, dimethyl sulfide can be oxidized as follows:
[edit] Preparation
Thioethers are typically prepared by the alkylation of thiols. An alternative method of synthesis includes the addition of a thiol to an alkene:
- R-CH=CH2 + HS-R' → R-CH2-CH2-S-R'
Thioethers can also be prepared via the Pummerer rearrangement.
[edit] References
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| Functional groups |
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| Chemical class: Alcohol • Aldehyde • Alkane • Alkene • Alkyne • Amide • Amine • Azo compound • Benzene derivative • Carboxylic acid • Cyanate • Ester • Ether • Haloalkane • Imine • Isocyanide • Isocyanate • Ketone • Nitrile • Nitro compound • Nitroso compound • Peroxide • Phosphoric acid • Pyridine derivative • Sulfone • Sulfonic acid • Sulfoxide • Thioether • Thiol • Toluene derivative |
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