Hydroxythioéthers éthyléniques: synthèse et réarrangement spontané
Keyword(s):
Reactions of vinyloxiranes and thiophénols or phenylthiotrimethyl silane with ZnI2 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.
1979 ◽
Vol 101
(8)
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pp. 2239-2240
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Iron-catalysed oxidation of bisulphite aqueous solution: Evidence for a free radical chain mechanism
1994 ◽
Vol 28
(15)
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pp. 2549-2552
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1999 ◽
Vol 64
(6)
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pp. 971-976
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