Artículo
Rearomatization of trifluoromethyl sulfonyl dihydropyridines: Thermolysis vs photolysis
Firpo, Guadalupe
; Cooke, María Victoria
; Peláez, Walter José
; Chans, Guillermo Manuel
; Argüello, Gustavo Alejandro
; Gómez, Elizabeth; Alvarez Toledano, Cecilio
Fecha de publicación:
12/2017
Editorial:
John Wiley & Sons Ltd
Revista:
Journal Of Physical Organic Chemistry
ISSN:
0894-3230
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
In this article, we describe the static gas-phase pyrolysis, microwave-induced pyrolysis, and photolysis reactions of trifluoromethyl sulfonyl dihydropyridines. The goal of this work was to find a methodology that allows obtaining of substituted pyridines-which are known to be difficult to synthesize-to be reused in a new substitution reaction. We demonstrated that it is possible to achieve the rearomatization process by the elimination of the trifluoromethyl sulfonyl moiety through the 3 processes, with the static pyrolysis being the best method to obtain the substituted pyridines. In addition, we propose the 1,4-elimination (CF3SO2 + H) as the first step, since it is the less energetic process, as has also been corroborated by calculations. A competitive reaction (CO2 extrusion) also occurs, yielding undesired products. Copyright
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Articulos(INFIQC)
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Citación
Firpo, Guadalupe; Cooke, María Victoria; Peláez, Walter José; Chans, Guillermo Manuel; Argüello, Gustavo Alejandro; et al.; Rearomatization of trifluoromethyl sulfonyl dihydropyridines: Thermolysis vs photolysis; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 2017; 12-2017; 1-12
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