Abstract
Electron ionization-induced loss of SO2 from 2-nitrodiphenyl sulfide leads to the same ionic structure, or mixture of structures, as loss of N2 from the molecular ion of N1-phenylbenzotriazole. Ab initio calculations are in favor of the [C6H4—N—C6H5]+• distonic nitrenium radical cation instead of the N-phenylbenzo-Δ2-azirinium structure for the product ion. Collisionally activated dissociation mass-analyzed ion kinetic energy (CAD-MIKE) spectra of the four chloro isomers [3- or 4-Cl—C6H3—N—C6H5]+• and [C6H4—N—C6H4-3 or 4-Cl]+• show that these ions are non-interconverting structures and eliminate regioselectively their nitrene moiety. Comparison with the CAD-MIKE spectra of the product ions of the elimination of N2 from N1–3(or 4)-chlorophenylbenzotriazoles demonstrates that the loss of SO2 from 2-nitrophenyl aryl sulfides occurs in the gas phase via an ipso rearrangement involving a [1,4] migration of the aryl group. © 1998 John Wiley & Sons, Ltd.
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