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Novel Route to Triethylsilyl-Substituted Cyclopropanes

Abstract : Radical adducts of S-α-ketonyl dithiocarbonates (xanthates) to triethyl vinylsilane are converted into triethylsilyl-substituted cyclopropanes upon ozonolysis followed by exposure to 1,4-dibromobutane and Cs2CO3/18-crown-6 in refluxing acetonitrile. The sequence works best with phenacyl type adducts, and the use of the less bulky trimethysilyl (TMS) derivatives results in extensive desilylation.
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https://hal-polytechnique.archives-ouvertes.fr/hal-01102507
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Submitted on : Monday, January 12, 2015 - 8:52:42 PM
Last modification on : Thursday, March 5, 2020 - 6:30:30 PM

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Shi-Guang Li, Samir Z. Zard. Novel Route to Triethylsilyl-Substituted Cyclopropanes. Organic Letters, American Chemical Society, 2014, 16 (23), pp.6180-6183. ⟨10.1021/ol503081b⟩. ⟨hal-01102507⟩

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