PERFLUOROALKYL DERIVATIVES OF NITROGEN. PART LI. REACTION OF THE N-HALOHENOBISTRIFLUOROMETHYLAMINES (CF3)2NX (X=Cl, Br) WITH NORBORNADIENE

Article abstract of DOI:10.1016/S0022-1139(00)81518-3

Reaction of the amines (CF3)2NX (X=Cl, Br) with norbornadiene either in solvent (CH2Cl2) at -78 deg C in the dark or in the vapour phase at 20 deg C in daylight gives a mixture of 3-halogeno-5-(NN-bistrifluoromethylamino)nortricyclene (exo, endo- and exo, exo-isomers) and exo-5-(NN-bistrifluoromethylamino)-anti-7-halogenonorbornene in quantitative yield formed via halonium ion addition to the diene.The reaction of the amine (CF3)2NBr in solvent Me2O or Et2O at -78 deg C in the dark gives the same products in low yield, together with 3-bromo-5-alkoxynortricyclene (exo, endo- and exo, exo-isomers) and the amine (CF3)2NR (R=Me, Et) in high yield.