Three-component reaction between secondary phosphine sulfides, elemental selenium and vinyl ethers: the first examples of Markovnikov addition of thioselenophosphinic acids to double bond

Thioselenophosphinic acids, R2P(Se)SH, generated in situ from secondary phosphine sulfides and elemental selenium, easily add to various vinyl ethers (equimolar ratio, 100 °C, 1,4-dioxane, up to 40 min) to give earlier unknown S- and Se-[1-(organyloxy)ethyl]thioselenophosphinates, i.e., R2P(Se)SCH(M...

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Bibliographic Details
Published in:Tetrahedron 2013-07, Vol.69 (30), p.6185-6195
Main Authors: Oparina, Ludmila A., Artem'ev, Alexander V., Vysotskaya, Oksana V., Kolyvanov, Nikita A., Bagryanskaya, Irina Yu, Doronina, Evgeniya P., Gusarova, Nina K.
Format: Article
Language:English
Subjects:
Aromatic compounds
Bonding
Phosphines
Secondary phosphine sulfides
Selenium
Sulfides
Tetrahedrons
Thioselenophosphinic acids
Vinyl ethers
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Summary:Thioselenophosphinic acids, R2P(Se)SH, generated in situ from secondary phosphine sulfides and elemental selenium, easily add to various vinyl ethers (equimolar ratio, 100 °C, 1,4-dioxane, up to 40 min) to give earlier unknown S- and Se-[1-(organyloxy)ethyl]thioselenophosphinates, i.e., R2P(Se)SCH(Me)OR′ and R2P(S)SeCH(Me)OR′ (R, R′=alkyl, aralkyl, hetaralkyl and aryl), the S-esters being predominant (73–95% total yield). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.05.038