Synthesis of functionalized m-bistrifluoromethylbenzenes via cyclocondensation of 1,1,1,5,5,5-hexafluoroacetylacetone with enamines

• Published in: Tetrahedron Vol. 61; no. 11; pp. 2839 - 2847
• Main Authors: Volochnyuk, Dmitriy M., Kostyuk, Alexander N., Sibgatulin, Dmitriy A., Chernega, Alexander N.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 14-03-2005
• Subjects: 1,1,1,5,5,5-Hexafluoroacetylacetone; Cyclocondensation; Push–pull enamines; Trifluoromethylated benzenes; Push–pull enamines; Cyclocondensation; Trifluoromethylated benzenes; 1,1,1,5,5,5-Hexafluoroacetylacetone
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2005.01.075

The reaction of 1,1,1,5,5,5-hexafluoroacetylacetone with push–pull enamines having a methyl group at the α-position was investigated. It was found that the reaction is sensitive both to the structure of enamines and to reaction conditions. As a result, a set of bistrifluoromethyldialkylanilines and ethyl bistrifluoromethylsalicylate was prepared. Plausible mechanisms and factors influencing the course of the reaction are discussed.
Graphical Abstract