The preparation of nortropane N-oxyl (8-azabicyclo[3.2. 1]octane N-oxyl) and some homologs and derivatives is described. This radical oxidizes hydrogen peroxide and 2-propanol; labeling studies show that the bridgehead protons are not involved in these reactions. Nortropane N-oxyl dimerizes irreversibly in several solvents to give a product resulting from attack at a bridgehead position. In benzene at temperatures from 10 to 65°, the rate of this reaction is described by the equation kdec = 1010.9 exp(-21,700 plusmn; 1800 cal/RT) M-1 sec-1. The homolog, 9-azabicyclo[3.3.1]nonane N-oxyl, decays very much more slowly. In benzene at 30° this decay appears to be a first- rather than a second-order process.
Journal of the American Chemical Society95, no. 19 (1973): 6395–6400.