A Simple Atom-Economic Synthesis
of Functional Tertiary Phosphine Chalcogenides Bearing
Furan or Tetrahydrofuran Rings

Ludmila A. Oparina; Svetlana F. Malysheva; Nina K. Gusarova; Nataliya A. Belogorlova; Oksana V. Vysotskaya; Andrey V. Stepanov; Alexander I. Albanov; Boris A. Trofimov

doi:10.1055/s-0029-1216964

PAPER

A Simple Atom-Economic Synthesis of Functional Tertiary Phosphine Chalcogenides Bearing Furan or Tetrahydrofuran Rings

Ludmila A. Oparina, Svetlana F. Malysheva, Nina K. Gusarova, Nataliya A. Belogorlova, Oksana V. Vysotskaya, Andrey V. Stepanov, Alexander I. Albanov, 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) 4193461; e-Mail: gusarova@irioch.irk.ru;

Abstract

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Abstract

The first examples of hydrophosphorylation reactions of vinyl ethers of a series of furans are reported. Regiospecific addition of secondary phosphines, phosphine sulfides, or phosphine selenides to 2-[(vinyloxy)methyl]furan, 2-[1-(vinyloxy)butan-2-yl]furan, or 2-[(vinyloxy)methyl]tetrahydrofuran proceeds under UV irradiation to give the corresponding anti-Markovnikov adducts in 72-99% yield.

Key words

ethers - phosphines - phosphorylation - radical reaction - photochemistry

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References

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