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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Novel route to triethylsilyl-substituted cyclopropanes
1Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, 91128 Palaiseau Cedex, France.
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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