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What products form when thiols are oxidized?
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organosulfur compound
Examples of organosulfur compounds.
The oxidation of thiols leads to several different products depending on the reaction conditions and the structure of the thiol:
- Disulfides: The initial oxidation of thiols typically yields disulfides. These can also be formed through the combination of thiyl radicals.1
- Sulfenic acids: In the case of sterically hindered thiols, sulfenic acids (R—SO—H) can be isolated as the first-formed oxidation product. These compounds subsequently react with additional thiols to form disulfides.1
- Sulfonic acids: The oxidation of various organosulfur compounds, including thiols, is one of the methods used to prepare sulfonic acids (RSOH).2
Practical applications of these oxidation reactions include the neutralization of foul-smelling low-molecular-weight thiols using bleach (sodium or calcium hypochlorite) and the "sweetening" process in petroleum refining, where thiols in crude oil are oxidized into more innocuous disulfides.1