Sulfoxidation

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in chemistry, sulfoxidation refers to two distinct reactions.

Contents

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 + SO2 + ½ O2 → RSO3H

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.

R2S + O → R2SO

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:

(C6H5)2S + 2 H2O2 → (C6H5)2SO2 + 2 H2O

Many oxidants have been demonstrated, but from the perspective of green chemistry, hydrogen peroxide is favored. [4]

References

  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.
  4. ↑ 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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