Abstract
The free-radical halogenation of norbornane gives mainly the 2-halides; exo/endo ratios depending on the nature of the halogen donor. Molecular chlorine or bromine give about 70 per cent of exo- and 20–25 per cent of endo-halides: SO2Cl2, CCl4, PCl5 and CBrCl3 give 95 per cent of the exo-isomer. This increased stereospecificity is ascribed to the relatively lower accessibility of the intermediate 2-norbornyl radicals from the endo-side for the bulkier reagents. A small proportion of the 7-chloride was observed in the chlorinations with Cl2, SO2Cl2 and PCl5; the bridgehead chloride (1) could not be detected. Competitive halogenations of norbornane and cyclohexane indicate that the methylene groups in cyclohexane and in the six-membered ring of norbornane are about equally reactive towards various attacking radicals.
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