Atom-Economic Synthesis of Tris[2-(organylthio)ethyl]phosphine Oxides from Phosphine and Vinyl Sulfides

Nina K. Gusarova A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Nina I. Ivanova A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Maria V. Bogdanova A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Lidiya M. Sinegovskaya A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Alexander V. Gusarov 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

Abstract

Phosphine, generated from elemental phosphorus in the system KOH-toluene-H₂O, reacts with vinyl sulfides under free radical conditions (AIBN, dioxane, 65–70°C, atmospheric pressure) to form regiospecifically tris[2-(organylthio)ethyl]phosphines, which are readily oxidized in air to corresponding tris[2-(organylthio)ethyl]phosphine oxides.

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Financial support from the Ministry of Industry, Science and Technologies of Russian Federation (Grant No. NSH-2241.2003.3) and Russian Foundation for Basic Research (Grant No. 04-03-32045-a) is gratefully acknowledged.

Notes

^aSpectra of compounds 2a–c were taken in microlayer, spectra of products 2d were run in KBr.

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Atom-Economic Synthesis of Tris[2-(organylthio)ethyl]phosphine Oxides from Phosphine and Vinyl Sulfides

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Atom-Economic Synthesis of Tris[2-(organylthio)ethyl]phosphine Oxides from Phosphine and Vinyl Sulfides

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