Intramolecular competitive addition of vinyl radicals to keto and alkenyl groups in Wieland–Miescher ketones—synthesis of carbocycles and propellanes
Abstract
Wieland–Miescher ketone analogues are prepared by monoalkylation of cyclohexane-1,3-dione with bromomethylcycloalkenyl bromides followed by annulation with methyl vinyl ketone; they undergo 5-exo-trig competitive intramolecular radical addition to the keto and enone olefins to give angularly rused carbocycles and propellanes, respectively.