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Synthesis 2005(18): 3103-3106  
DOI: 10.1055/s-2005-918408
PAPER
© Georg Thieme Verlag Stuttgart · New York

Hydrothiophosphorylation of Vinyl Sulfoxides: First Examples

Nina K. Gusarovaa, Maria V. Bogdanovaa, Nina I. Ivanovaa, Nataliya A. Chernyshevaa, Boris G. Sukhova, Lidiya M. Sinegovskayaa, Olga N. Kazhevab, Grigorii G. Alexandrovc, Oleg A. D’yachenkob, Boris A. Trofimov*a
a A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia
Fax: +7(3952)419346; e-Mail: gusarova@irioch.irk.ru;
b Institute of Problems of Chemical Physics RAS, 1 Semenov Av., 142432 Chernogolovka, Russia
c Kurnakov Institute of General and Inorganic Chemistry RAS, 31 Leninskii Av., 119991 Moscow, Russia
Further Information

Publication History

Received 3 May 2005
Publication Date:
12 October 2005 (online)

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Abstract

The first examples of facile hydrothiophosphorylation of organyl vinyl sulfoxides are described. Nucleophilic addition of P,S-ambident secondary phosphine sulfides 1 and 2 to organyl vinyl sulfoxides 3-6 with potassium hydroxide at room temperature proceeds chemo- and regioselectively to give the corresponding bis(2-organylethyl)[2-(organylsulfinyl)ethyl]phosphine sulfides 7a-e in high isolated yields.

Key words

hydrothiophosphorylations - vinyl sulfoxides - secondary phosphine sulfides - nucleophilic additions

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