EPR and mass spectroscopic identification of radical adducts produced spontaneously from reactions of phosgene, chlorine gas and bromine with C-phenyl N-tert-butyl nitrone (PBN)

Abstract

The toxic gas phosgene reacts with the spin trap C-phenyl N-tert-butyl nitrone (PBN) to produce spontaneously N-tert-butyl-N-chloroacylaminoxyl as the main radical product identified by EPR and mass spectrometry. The reaction mechanisms for the formation of N-tert-butyl-N-chloroacylaminoxyl and other radicals are proposed. Reactions of chlorine gas and bromine with PBN have also been investigated. First α-chloro- or α-bromo-PBN is formed followed by chlorination or bromination of the aryl ring of these compounds, respectively.