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Synthesis 2008(17): 2743-2746  
DOI: 10.1055/s-2008-1067212
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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;
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Publication History

Received 28 April 2008
Publication Date:
06 August 2008 (online)

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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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