Electrochemical behaviour of oxaziridines at the mercury electrode in organic solvent

The electrochemical behaviour of 2-methylsulphonyl-3-phenyloxaziridine (1) and 2-t-butyl-3-phenyloxaziridine (2) has been investigated by polarograhic techniques in aprotic solvent. The electroreductive center appears to be the oxaziridine ring but the rearrangement following the electron uptake yields benzaldehyde and imine for the derivatives (1) and (2) respectively. This peculiar behaviour has been discussed on the basis of calculated theoretical indices (CNDO/2 method), like energy values and shapes of frontier molecular orbitals, which suggest the N-O bond breaking as the first step of the overall reduction process.The electrochemical behaviour of 2-methylsulphonyl-3-phenyloxaziridine (1) and 2-tbutyl-3-phenyloxaziridine (2) has been investigated by polarographic techniques in aprotic solvent. The electroreductive center appears to be the oxaziridine ring but the rearrangement following the electron uptake yields benzaldehyde and imine for the derivatives (1) and (2) respectively. This peculiar behaviour has been discussed on the basis of calculated theoretical indices (CNDO/2 method), like energy values and "shapes" of frontier molecular orbitals, which suggest the NO bond breaking as the first step of the overall reduction process. © 1990