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Tandem mass spectrometry (MS/MS) has been applied to investigate the behaviour of 1-(2-nitrophenyl)benzotriazole [8] upon flash-vacuum pyrolysis (FVP) conditions. Above 500°, 8 is pyrolyzed to give a mixture of 1-nitrocarbazole [11], 1-hydroxycarbazole [12] and carbazole [13] Under similar conditions, 2-(2-nitrophenyl) benzotriazole [9] appears to be more stable; it is however partially isomerized into 8 at high temperatures. Aza analogs of 8, like 1-(2-nitro-4-pyridyl) benzotriazole [10] also loose nitrogen above 500° to give a mixture of 1-nitro-3-azacarbazole [19], 1-hydroxy-3-azacarbazole [16] and 3-azacarbazole [17]. |
