CYCLIC VOLTAMMETRY AND ELECTRON-PARAMAGNETIC-RESONANCE STUDY OF THE ELECTROCHEMICAL REDUCTION OF P-NITROBENZYL BROMIDE IN APROTIC-SOLVENTS

EPR has been used to investigate the radicals postulated as intermedia tes in the intramolecular electron transfer and dehalogenation of p-ni trobenzyl bromide (p-NBBr) in DMSO and DMFA at room temperature. The e lectrochemical behavior has been studied through the use of cyclic vol tammetry. According to the postulated reaction mechanism, the one-elec tron reduction of p-nitrobenzyl bromide generates an anion radical whi ch undergoes breakage of the C-Br bond followed by intramolecular elec tron transfer. The free radical obtained is finally transformed into p -nitrotoluene.