Generation and intermolecular capture of cyclopropylacyl radicals.
[reaction: see text] 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 beta-elimination of the xanthate group.
Heinrich
Markus R
MR
Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, 91128 Palaiseau Cedex, France.
Zard
Samir Z
SZ