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Rearomatization of trifluoromethyl sulfonyl dihydropyridines: Thermolysis vs photolysis
Author(s) -
Firpo Guadalupe,
Cooke María V.,
Peláez Walter J.,
Chans Guillermo M.,
Argüello Gustavo A.,
Gómez Elizabeth,
AlvarezToledano Cecilio
Publication year - 2019
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3789
Subject(s) - chemistry , trifluoromethyl , sulfonyl , moiety , photodissociation , pyrolysis , thermal decomposition , computational chemistry , organic chemistry , alkyl
Abstract 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 (CF 3 SO 2 + H) as the first step, since it is the less energetic process, as has also been corroborated by calculations. A competitive reaction (CO 2 extrusion) also occurs, yielding undesired products.