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Synthesis 2002(15): 2207-2210
DOI: 10.1055/s-2002-34852
PAPER
© Georg Thieme Verlag Stuttgart · New York

Hydrophosphination of Vinyl Sulfides and Vinyl Selenides: First Examples

Boris A. Trofimov, Nina K. Gusarova*, Svetlana F. Malysheva, Nina I. Ivanova, Boris G. Sukhov, Natal’ya A. Belogorlova, Vladimir A. Kuimov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky Street 1, 664033 Irkutsk, Russia
Fax: +7(3952)396046; e-Mail: gusarova@irioch.irk.ru;
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Publication History

Received 30 April 2002
Publication Date:
21 October 2002 (online)

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Abstract

The first examples of the hydrophosphination of alkyl vinyl sulfides and selenides are described. The reaction of secondary phosphines (R1)2PH 1-3 with vinyl chalcogenides CH2=CHXR2 4-9 proceeds readily under radical initiation to give in anti-Markovnikov mode regiospecifically the corresponding organylchalcogenophosphines (R1)2PCH2CH2XR2 10a-h in high yields.

Key words

phosphines - sulfur - selenium - phosphorus - addition reactions - radicals

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