Regio- and chemo-selectivity of adamantane halogenation by Gif-Barton and metalloporphyrin catalysis and by classical free-radical reactions

The halogenation of adamantane by CBrCl3 with Gif-Barton and metalloporphyrin catalysis is compared with classical free-radical halogenations (Br2, NBS, t-BuOCl, R2NCl) and with the behaviour of simple alkanes (n-hexane, 2,3-dimethylbutane, cyclohexane); the free-radical mechanism is discussed.