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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 185, 2010 - Issue 9
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Original Articles

One-Pot Vinylation of Secondary Phosphine Chalcogenides with Vinyl Sulfoxides

Svetlana F. Malysheva A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia
,
Nina K. Gusarova A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia
,
Natal'ya A. Belogorlova A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia
,
Tamara V. Kashik A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia
,
Leonid B. Krivdin A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia
,
Sergei V. Fedorov A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia
&
Boris A. Trofimov A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia
 show all
Pages 1838-1844 | Received 25 Jun 2009, Accepted 03 Sep 2009, Published online: 25 Aug 2010
 
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Abstract

A facile, one-pot vinylation of secondary phosphine chalcogenides with alkyl(or aryl) vinyl sulfoxides has been elaborated. The vinylation comprises the nucleophilic addition of secondary phosphine chalcogenides to the vinyl sulfoxides (∼50 mol% KOH, dioxane, 25–40°C, 1 h) followed by the elimination of sulfenic acids from the adducts (additional equivalent of KOH, 60–70°C, 1.5–2.0 h), the yields of target tertiary vinyl phosphine chalcogenides reaching 92%.

Acknowledgments

Financial support from the Russian Foundation for Basic Research (grants no. 07-03-00562 and 08-03-00021) is gratefully acknowledged.

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