Radical Addition of Secondary
Phosphine Sulfides and Selenides to Vinyl Selenides

Nina K. Gusarova; Nataliya A. Chernysheva; Svetlana V. Yas’ko; Tatyana I. Kazantseva; Igor A. Ushakov; Boris A. Trofimov

doi:10.1055/s-2008-1067212

PAPER

Radical Addition of Secondary Phosphine Sulfides and Selenides to Vinyl Selenides

Nina K. Gusarova, Nataliya A. Chernysheva, Svetlana V. Yas’ko, Tatyana I. Kazantseva, Igor A. Ushakov, Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russian Federation
Fax: +7(3952)419346; e-Mail: gusarova@irioch.irk.ru;

Abstract

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Abstract

The first examples of a facile hydrochalcogenophosphorylation of alkyl vinyl selenides are reported. The regiospecific addition of secondary phosphine sulfides and phosphine selenides to vinyl selenides proceeds under radical initiation (AIBN, 65-70 ˚C, 1 h or UV-irradiation, 1 h) to afford the anti-Markovnikov adducts in 87-95% yield.

Key words

alkyl vinyl selenides - secondary phosphine sulfides - secondary phosphine selenides - radical addition - functional tertiary phosphine chalcogenides

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References

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