Journal of Organic Chemistry p. 190 - 195 (1992)
Update date:2022-09-26
Topics:
Katritzky, Alan R.
Ji, Fu-Bao
Fan, Wei-Qiang
Gallos, John K.
Greenhill, John V.
et al.
A variety of mono- and diarylsulfonyl-substituted 4-aminobenzotriazoles were prepared.Thermal rearrangements of 4-amino-1-(arylsulfonyl)benzotriazoles to 4-<(arylsulfonyl)amino>benzotriazoles were observed and confirmed by separation of the rearrangement products.Their structures were characterized by spectral methods and by X-ray crystallography.The rearrangement rates were studied by variable-temperature NMR experiments.Crossover experiments support an intramolecular mechanism involving a heterolytic benzotriazole ring cleavage to form a diazo intermediate followed by recyclization to the 4-amino group.
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