EPR AND MASS SPECTROSCOPIC IDENTIFICATION OF RADICAL ADDUCTS PRODUCEDSPONTANEOUSLY FROM REACTIONS OF PHOSGENE, CHLORINE GAS AND BROMINE WITH C-PHENYL N-TERT-BUTYL NITRONE (PBN)

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