The triazenols 4-R(1)-C6H4-N=N-N(OH)-R(2) (1), oxidized with t-BuO(2)(
.) radicals, produced nitroxide radicals R(1)-C6H4-N(O-.)-N=N(R(2))O-(-) (5). The suggested radical structure was confirmed by N-15-labelin
g. The reaction of triazenols 1 with PbO2 proceeded under N-2 eliminat
ion, in which case nitroxides R(1)-C6H4-N(R(2))-O-. (2) were observed
as the final radical products. The intermediate R(1)-C6H4. radicals we
re identified by spin-trapping.