Physics:Sulfoxidation
in chemistry, sulfoxidation refers to two distinct reactions.
Reactions of alkenes with sulfur dioxide
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]
- RH + SO
2 + ½ O
2 → RSO
3H
The reaction favors secondary positions in accord with its free-radical mechanism. Mixtures are produced. Semiconductor-sensitized variants have been reported.[2]
Oxidation of sulfides
Sulfoxidation can also refer to the oxidation of a thioether to a sulfoxide.
- R
2S + O → R
2SO
For unsymmetrical sulfides, the sulfoxide will be chiral. Significant effort have led to asymmetric versions of the sulfide to sulfoxide reaction..[3] Sulfoxides can be further oxidized to sulfones, as illustrated with diphenylsulfone:
- (C
6H
5)
2S + 2 H
2O
2 → (C
6H
5)
2SO
2 + 2 H
2O
Many oxidants have been demonstrated, but from the perspective of green chemistry, hydrogen peroxide is favored.[4]
References
- ↑ Kosswig, Kurt (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a25_503.
- ↑ 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". Coordination Chemistry Reviews 257 (21–22): 3030–3050. doi:10.1016/j.ccr.2013.05.010. https://hal.archives-ouvertes.fr/hal-00865625/file/CCR_2_Simonneaux-accepted.pdf.
- ↑ Sato, Kazuhiko; Hyodo, Mamoru; Aoki, Masao; Zheng, Xiao-Qi; Noyori, Ryoji (2001). "Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions". Tetrahedron 57 (13): 2469–2476. doi:10.1016/s0040-4020(01)00068-0.
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