title: Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles.
abstract: 2-Aryl-1,2,3-triazoles were synthesized by cyclization of the corresponding glyoxal arylosazones, generated from commercial arylhydrazines. The deproto-metallation of 2-phenyl-1,2,3-triazole was attempted using different 2,2,6,6-tetramethylpiperidino-based mixed lithium-metal (Zn, Cd, Cu, Co, Fe) combinations, giving results in the case of Zn, Cd, and Cu. The lithium-zinc combination was next selected to apply the deprotonation-iodination sequence to all the 2-aryl-1,2,3-triazoles synthesized. The results were analyzed with the help of the CH acidities of the substrates, determined in THF solution using the DFT B3LYP method.
authors.affiliation: Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS- Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, 35042 Rennes, France. floris.chevallier@univ-rennes1.fr
authors.forename: Floris
authors.initials: F
authors.lastname: Chevallier
authors.forename: Thomas
authors.initials: T
authors.lastname: Blin
authors.forename: Elisabeth
authors.initials: E
authors.lastname: Nagaradja
authors.forename: Frédéric
authors.initials: F
authors.lastname: Lassagne
authors.forename: Thierry
authors.initials: T
authors.lastname: Roisnel
authors.forename: Yury S
authors.initials: YS
authors.lastname: Halauko
authors.forename: Vadim E
authors.initials: VE
authors.lastname: Matulis
authors.forename: Oleg A
authors.initials: OA
authors.lastname: Ivashkevich
authors.forename: Florence
authors.initials: F
authors.lastname: Mongin
mesh_terms: D000143:Acids / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis*
chemical_list: D000143:Acids; D008670:Metals; D014230:Triazoles