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On the mechanism of the diazirine exchange reaction with azide anion

1989; Elsevier BV; Volume: 30; Issue: 37 Linguagem: Inglês

10.1016/s0040-4039(01)80537-2

1873-3581

Kathleen E. Bainbridge, William P. Dailey,

Synthesis and Catalytic Reactions

Treatment of isotopically labeled bromophenyldiazirine containing one 15N atom with azide ion produces benzonitrile which contains 50% 15N. This suggests that N-azidodiazirines are intermediates in the reaction. Ab initio calculations predict that N-azidodiazirines will have a very low barrier to decomposition to nitrile and two molecules of nitrogen.