Hydroxythioéthers éthyléniques: synthèse et réarrangement spontané

Hydroxythioéthers éthyléniques: synthèse et réarrangement spontané

Reactions of vinyloxiranes and thiophénols or phenylthiotrimethyl silane with ZnI 2 or n BuLi, at room temperature, were studied. These condensations proceed regio and stereospecifically to afford, in good yields, three families of hydroxy aryl ethylenic sulfides. The regiochemistry is determined by...

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Veröffentlicht in:Canadian journal of chemistry 1992-08, Vol.70 (8), p.2190-2196
Hauptverfasser: Martin, Ghislaine, Sauleau, Jean, David, Michèle, Sauleau, Armelle, Sinbandhit, Sourisak
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container_end_page 2196
container_issue 8
container_start_page 2190
container_title Canadian journal of chemistry
container_volume 70
creator Martin, Ghislaine
Sauleau, Jean
David, Michèle
Sauleau, Armelle
Sinbandhit, Sourisak
description Reactions of vinyloxiranes and thiophénols or phenylthiotrimethyl silane with ZnI 2 or n BuLi, at room temperature, were studied. These condensations proceed regio and stereospecifically to afford, in good yields, three families of hydroxy aryl ethylenic sulfides. The regiochemistry is determined by the stereochemistry, the substitution of the oxiranes, and the reaction conditions. During the condensation, 1,3 phenylthio migration occurs. Light initiates the rearrangement by bringing about cleavage of the allyl sulfur bond — a radical chain mechanism — of the hydroxy allylphenyl sulfides. Scope, rate constants, and product composition of the rearrangement were studied.
doi_str_mv 10.1139/v92-274
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title Hydroxythioéthers éthyléniques: synthèse et réarrangement spontané
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