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Keywords:

  • azo compounds;
  • benzotriazoles;
  • oxidative addition reactions;
  • rearrangement;
  • transition metals;
  • vibrational spectroscopy

Abstract

The in situ observation of benzotriazole ring and ring-opened isomers, which result from the Dimroth equilibrium for 1-[(nonafluorobutane)sulfonyl]benzotriazole, 1, in solution by 19F NMR and UV/Vis spectroscopy is reported. Two benzotriazoles, compound 1 and 1,1′-sulfonylbis(benzotriazole) (3), undergo Dimroth triazole ring opening and coordination to an iridium(I) metal center to give either linear diazo [IrI1-NNPhNSO2C4F9)(Cl)(PPh3)2] (2) or an unusual double bent diazene [IrIII3-NNPhNSO2Btz)(Cl)(PPh3)2] (4; Btz=benzotriazole) complex.