Halogenation of dehydronoriceane (1) in dichloromethane in the dark exclusively or predominantly gave the trans-4,5-dihalogenoethanonoradamantanes (2) providing decisive evidence for front side attack on the bicyclo[2.1.0]pentane system by halonium ions; the reaction is susceptible to the solvent and halogen used.
T. Katsushima, R. Yamaguchi, S. Iemura and M. Kawanisi, J. Chem. Soc., Chem. Commun., 1980, 133 DOI: 10.1039/C39800000133
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