Electron paramagnetic resonance study of the reactions of the spin trap 2,4,6-tribromonitrosobenzene in benzene solutions

Abstract

By means of static-sample studies involving the thermal decomposition of symmetric azo compounds and the oxidation of substrates with nickel peroxide, we have characterized by electron paramagnetic resonance 12 spin adducts of 2,4,6-tribromonitrosobenzene, 1, in benzene at 25 °C. In addition, we have used electron paramagnetic resonance spectroscopy to investigate benzene solutions of 1 both by itself and in the presence of olefins, and both in the presence and absence of light. Although 1 by itself did not give evidence for any free radical formation, when 1 was mixed with any one of the 11 olefins tested we could detect nitroxide formation. The presence of light did not affect our results. These observations support the "ene" reaction mechanism of nitroxide formation. Keywords: 2,4,6-tribromonitrosobenzene, spin trapping, nickel peroxide.