Abstract
When tri-, di- and monohalomethyl radicals are generated photo-chemically in the presence of 2-nitroso-2-methylpropane the expected ESR spectra of the (poly)halomethyl t-butyl nitroxides are normally only observed when the halogen atom is fluorine (see chapter 2) and not when it is chlorine, bromine or iodine. These nitroxides are often very unstable. Apparently, β-halogen elimination occurs easily (except for fluorine) to give halonitrones. These halonitrones may act as precursors for the formation of new types of acyl alkyl nitroxides, which are actually observed (a N = 6.5–7.0 gauss). A mechanism is proposed in which the halonitrones undergo light-induced isomerization to halo-oxaziridines followed by a bimolecular oxidation-reduction reaction leading to the observed acyl alkyl nitroxides.
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