title: Synthesis of 1,3-diaryl-3-trifluoromethylcyclopropenes by transition-metal-free reaction of 2,2,2-trifluoroacetophenone tosylhydrazones with alkynes: the effect of the trifluoromethyl group.
abstract: 1,3-Diaryl-3-trifluoromethylcyclopropenes and 2-aryl- or 2-alkyl-1,3-diaryl-3-trifluoromethylcyclopropenes are prepared in a very simple way by reaction between 1,1,1-trifluoroacetophenone tosylhydrazones and terminal or internal alkynes, respectively, in a base promoted process that does not require the presence of any metal catalyst. The essential role of the trifluoromethyl group, which enables the formation of the cyclopropenes instead of the expected pyrazoles, has been computationally investigated, suggesting the participation of a free carbene.
authors: Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, c/Julián Clavería 8, Oviedo, 33006, Spain. pcabal@uniovi.es acvg@uniovi.es.
authors: Raquel
authors: R
authors: Barroso
authors: Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, c/Julián Clavería 8, Oviedo, 33006, Spain. pcabal@uniovi.es acvg@uniovi.es.
authors: Azucena
authors: A
authors: Jiménez
authors: Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, c/Julián Clavería 8, Oviedo, 33006, Spain. pcabal@uniovi.es acvg@uniovi.es.
authors: M Carmen
authors: MC
authors: Pérez-Aguilar
authors: Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, c/Julián Clavería 8, Oviedo, 33006, Spain. pcabal@uniovi.es acvg@uniovi.es.
authors: María-Paz
authors: MP
authors: Cabal
authors: Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, c/Julián Clavería 8, Oviedo, 33006, Spain. pcabal@uniovi.es acvg@uniovi.es.
authors: Carlos
authors: C
authors: Valdés
mesh_terms: D000098:Acetophenones / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: D000098:Acetophenones; D000480:Alkynes; D003521:Cyclopropanes; D006845:Hydrocarbons, Fluorinated; D008670:Metals; D014105:Tosyl Compounds