Sulfoxidation

in chemistry, sulfoxidation refers to two distinct reactions.

In one meaning, sulfoxidation refers to the reaction of alkanes with a mixture of sulfur dioxide and oxygen. This reaction is employed industrially to produce alkyl sulfonic acids, which are used as surfactants. The reaction requires UV-radiation.^[1]

{\ce {RH + SO2 + 1/2 O2 -> RSO3H}}

The reaction favors secondary positions in accord with its free-radical mechanism. Mixtures are produced. Semiconductor-sensitized variants have been reported.^[2]

Sulfoxidation can also refer to the oxidation of a thioether to a sulfoxide.

{\ce {R2S + O -> R2SO}}

A typical source of "O" is hydrogen peroxide.^[3]

References

^ Kosswig, Kurt (2000). "Sulfonic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a25_503. ISBN 3527306730.
^ Parrino, Francesco; Ramakrishnan, Ayyappan; Kisch, Horst (2008). "Semiconductor-Photocatalyzed Sulfoxidation of Alkanes". Angewandte Chemie International Edition. 47 (37): 7107–7109. doi:10.1002/anie.200800326. PMID 18683178.
^ Srour, Hassan; Le Maux, Paul; Chevance, Soizic; Simonneaux, Gérard (2013). "Metal-Catalyzed Asymmetric Sulfoxidation, Epoxidation and Hydroxylation by Hydrogen Peroxide" (PDF). Coordination Chemistry Reviews. 257 (21–22): 3030–3050. doi:10.1016/j.ccr.2013.05.010.

[1] Kosswig, Kurt (2000). "Sulfonic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a25_503. ISBN 3527306730.

[2] Parrino, Francesco; Ramakrishnan, Ayyappan; Kisch, Horst (2008). "Semiconductor-Photocatalyzed Sulfoxidation of Alkanes". Angewandte Chemie International Edition. 47 (37): 7107–7109. doi:10.1002/anie.200800326. PMID 18683178.

[3] Srour, Hassan; Le Maux, Paul; Chevance, Soizic; Simonneaux, Gérard (2013). "Metal-Catalyzed Asymmetric Sulfoxidation, Epoxidation and Hydroxylation by Hydrogen Peroxide" (PDF). Coordination Chemistry Reviews. 257 (21–22): 3030–3050. doi:10.1016/j.ccr.2013.05.010.

[1]

[2]

[3]