Abstract
A series of 1-tosyl-substituted 4-arylcarbamoyl-1,2,3-triazol-2-olates, which can undergo rearrangement to isomeric 1-aryl-4-tosylcarbamoyl-1,2,3-triazol-5-olates and N-tosyl-N'-aryldiazomalonimidolates, were synthesized. An equilibrium between these compounds is observed in solutions in DMSO. The introduction of an electron-withdrawing substituent into the aryl residue increases the stability of the 1-tosyl-1,2,3-triazoles but reduces the stability of the 1-aryl-1,2,3-triazoles. π-Donating substituents increase the stability of the open-chain structure.
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Morzherin, Y.Y., Rozin, Y.A., Savel'eva, E.A. et al. Triple Equilibrium in N'-Aryl-N-tosyldiazomalonimidolates, 1-Tosyl-1,2,3-triazol-5-olates, and 1-Aryl-1,2,3-triazol-5-olates. Chemistry of Heterocyclic Compounds 39, 168–173 (2003). https://doi.org/10.1023/A:1023756005530
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DOI: https://doi.org/10.1023/A:1023756005530