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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.
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Rajamannar et al. (1994) studied this question.
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