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

Add time:09/24/2019    Source:sciencedirect.com

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).

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