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Synthesis 2009(19): 3332-3338  
DOI: 10.1055/s-0029-1216948
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Reaction of Secondary Phosphine Selenides with Selenium and Nitrogen Bases: A Novel Synthesis of Diorganodiselenophosphinates

Boris A. Trofimov*a, Alexander V. Artem’eva, Nina K. Gusarovaa, Svetlana F. Malyshevaa, Sergei V. Fedorova, Olga N. Kazhevab, Grigorii G. Alexandrovb, Oleg A. Dyachenkob
a A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation, Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;
b Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Academician N. N. Semenov Str., 142432 Chernogolovka, Russian Federation
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Publication History

Received 15 May 2009
Publication Date:
21 August 2009 (online)

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Abstract

A three-component reaction of secondary phosphine selenides­ R2P(Se)H [R = PhCH2CH2, PhCH(Me)CH2, 4-t-BuC6H4CH2CH2, (2-methyl-5-pyridyl)CH2CH2, Ph], elemental selenium, and primary, secondary, and tertiary amines and diamines proceeds under mild conditions (25-85 ˚C, 1-90 min) in tetrahydrofuran-ethanol as medium to give previously unknown mono-, di-, and triorganoammonium salts of diorganodiselenophosphinates in high yields (up to 99%).

Key words

secondary phosphine selenides - elemental selenium - amines - three-component atom-economic reactions - diselenophosphinates - phosphorus compounds

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