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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 17
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Original Articles

Solvent Effects in the Oxidation of Sulfides with NaBrO3/Mg(HSO4)2

Ahmad Shaabani Department of Chemistry, Medicinal and Aromatic Plants and Drug Research Institute, Shahid Beheshti University, Tehran, Iran; Department of Phytochemistry, Medicinal and Aromatic Plants and Drug Research Institute, Shahid Beheshti University, Tehran, IranCorrespondence[email protected]
,
Ayoob Bazgir Department of Chemistry, Medicinal and Aromatic Plants and Drug Research Institute, Shahid Beheshti University, Tehran, Iran
,
Kamal Soleimani Department of Chemistry, Medicinal and Aromatic Plants and Drug Research Institute, Shahid Beheshti University, Tehran, Iran
&
Peyman Salehi Department of Phytochemistry, Medicinal and Aromatic Plants and Drug Research Institute, Shahid Beheshti University, Tehran, Iran
Pages 2935-2944 | Received 19 Nov 2002, Published online: 21 Aug 2006
 
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Abstract

The oxidation of alkyl and aryl sulfides into the corresponding sulfoxides by NaBrO3/Mg(HSO4)2 is studied. The selectivity of the reactions are highly governed by the choice of solvents and reaction conditions. Both alkyl and aryl sulfides are efficiently oxidized in CH3CN and under solvent-free conditions, but in competition reactions with alkyl and aryl sulfides in CH3CN only alkyl sulfides are oxidized In n-hexane alkyl sulfides are oxidized to sulfoxides and oxidation of aryl sulfides completely inhibited.

Acknowledgment

Financial support by Research Council of Shahid Beheshti University is gratefully acknowledged.

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