Recycltzation of the imidazoline ring in nitroxyl radical derivatives of 3-imidazoline following oxidation by halogens and nitrous acid

Abstract

1. Nitroxyl radicals in 3-imidazoline 3-oxide are not oxidized by halogens, whereas nitroxyl radicals in 3-imidazoline react with chlorine, bromine, and nitrous acid with fission of the imidazoline ring. 2. 4-Carboxy-3-imidazoline-1-oxyls on treatment with bromine and nitrous acid undergo recyclization to 3-oxazolin-5-ones. 3. Bromine treatment of 4-formyl- and 4-acetyl-3-imidazolin-1-oxyl oximes results in recyclization to 2H-imidazole 1-oxides.