Annulation of the Cyclohexane Ring by Tandem Free Radical Alkylation of a Nonactivated δ-Carbon Atom−Intramolecular Carbanion Cycloalkylation

<UFIGR ID="ol0062401n00001">Annulation of the cyclohexane ring by a combination of free radical and ionic reactions sequences was achieved. Free radical alkylation of the remote nonactivated δ-carbon atom involves addition of δ-carbon radicals, generated by 1,5-hydrogen transfer in alkoxy radical intermediates, to radicophilic olefins, while the polar sequence involves enolate anions as intermediates which undergo a cycloalkylation reaction. Thus, the cyclohexane ring was constructed using diverse acyclic and cyclic structures as precursors of alkoxy radicals.