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Generation and Intermolecular Capture of Cyclopropylacyl Radicals

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journal contribution
posted on 23.12.2004, 00:00 by Markus R. Heinrich, Samir Z. Zard
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 β-elimination of the xanthate group.