Reaction of arylhalodiazirines with thiophenoxide: a redox process

X Creary, AF Sky, G Phillips…

Index: Creary, Xavier; Sky, Anthony F.; Phillips, Gillian; Alonso, David E. Journal of the American Chemical Society, 1993 , vol. 115, # 17 p. 7584 - 7592

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Citation Number: 21

Abstract

Abstract: Phenylbromodiazirine reacts with thiophenoxide ion in methanol to give benzonitrile, benzamidine, ammonia, and diphenyl disulfide. The reaction is general for arylhalodiazirines, with electron-withdrawing groups on the aromatic ring exerting a small rate-enhancing effect. Three potential mechanisms are suggested for this redox process. These mechanisms include an N-sulfenylated diazirine, a diazirinyl radical, and a ...