Abstract
N,N-dimethyl-3-noradamantanamine-N-oxide (5), a potential precursor of tricyclo[3.3.1.03,7]nonan-3(7) ene, has been synthesized in two steps involving an Eshweiler-Clark reaction of 3-noradamantanamine followed by m-chloroperoxybenzoic acid oxidation of the resulting N,N-dimethylamino-3-noradamantanamine (4). Thermolysis of 5, however, unexpectedly gave the reduced N,N-dimethylamino product, 4.