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Photolysis of the hindered N-Chloroamines, 1-chloro-2,2,6,6-tetramethyl-4-oxopiperidine (IIa), 1-chloro-2,2,6,6-tetramethylpiperidine (IIb), and 1-chloro-2,2,5,5-tetramethyl-4-oxoimidazolidine (IIc), in benzene solution were carried out in an ESR spectrometer cavity. The ESR spectra of the corresponding amino radicals IIIa, IIIb, and IIIc were observed in evacuated solutions. In solutions containing oxygen, it was found that amino radicals IIIb and IIIc, readily reacted with oxygen to give the corresponding stable nitroxide radicals IVb and IVc, from the shapes of spectra and g-values. Amino radical IIIa did not react with oxygen. Although the amino radicals could not be isolated, their formation was confirmed by the isolation of a coupling product with a benzyl radical generated from dibenzylmercury.

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