A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination

Abstract : An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.
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Submitted on : Wednesday, March 26, 2014 - 9:52:03 PM
Last modification on : Thursday, February 7, 2019 - 5:10:38 PM

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Kelvin Kau Kiat Goh, Sunggak Kim, Samir Zard. A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination. Journal of Organic Chemistry, American Chemical Society, 2013, 78 (23), pp.12274-12279. ⟨10.1021/jo402169v⟩. ⟨hal-00966617⟩

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