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Updated: Jun 30, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Stereochemical and Computational NMR Survey of 1,2,3-Triazoles: in Search of the Original Tauto-Conformers
Valentin A Semenov1, Lyudmila I Larina1
1A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky st. 1, Irkutsk 664033, Russia.
Abstract:
The conformational analysis of nine functionalized 1,2,3-triazoles was carried out by the correlation of calculated and experimental high-level nuclear magnetic resonance (NMR) chemical shifts. In solution, the studied triazoles are in exchange dynamic equilibrium caused by their prototropic tautomerism of the NH-proton. The experimentally unresolved NMR signals were assigned for most of the compounds. A more thorough survey was conducted for 4-t-butyl-1,2,3-triazole-5-carbaldehyde oxime. The analysis performed within the framework of the DP4+ formalism completely confirmed the hypothesis of the predominance of the 2H-tautomer. Thus, the methodology for estimating stereochemical structures in the absence of some experimental data allowed the most stable conformations for dynamic systems with different tautomeric ratios to be reliably identified.
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