Generation and intermolecular capture of cyclopropylacyl radicals

Abstract : (Chemical Equation Presented) Cyclopropylacyl radicals derived from S-cyclopropylacyl xanthates (dithiocarbonates) undergo intermolecular additions to olefins without loss of CO or ring opening. In the presence of a phenyl ring on carbon C-1 of the cyclopropane ring, loss can be made to occur in the absence of an olefinic trap. The adducts from the cyclopropylacyl radical additions are easily converted into enones by base-induced ß-elimination of the xanthate group.
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Markus Heinrich, Samir Zard. Generation and intermolecular capture of cyclopropylacyl radicals. Organic Letters, American Chemical Society, 2004, 6 (26), pp.4969-4972. ⟨10.1021/ol047892i⟩. ⟨hal-00954816⟩

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