Generation and intermolecular capture of cyclopropylacyl radicals

Markus R. Heinrich (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

(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.

Domaines: Chimie organique

Markus R. Heinrich, Samir Z. Zard. Generation and intermolecular capture of cyclopropylacyl radicals. Organic Letters, 2004, 6 (26), pp.4969-4972. ⟨10.1021/ol047892i⟩. ⟨hal-00954816⟩