182947-20-2Relevant academic research and scientific papers
Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes
Schneider, Thomas,Keim, Michael,Seitz, Bianca,Maas, Gerhard
, p. 2064 - 2072 (2020)
3-Aryl-1-(trifluoromethyl)prop-2-yn-1-iminium triflate salts represent a novel, highly reactive class of acetylenic iminium salts. Herein we present several reactions which are based on the electron-poor acetylenic bond and on the high electrophilicity of the CF3-substituted iminium group. These salts were found to be highly reactive dienophiles in Diels–Alder reactions with cyclopentadiene, 2,3-dimethylbutadiene and even anthracene. At higher temperature, the cycloadducts undergo an intramolecular SE(Ar) reaction leading to condensed carbocycles incorporating a 1-(trifluoromethyl)-1-(dimethylamine)indene ring system. With styrenes and some substituted styrenes, cascade reactions take place, which likely include cyclobutene and several cationic intermediates and mainly yield 2-(1-phenylvinyl)indenes. In a similar reaction cascade, a fulvene derivative was obtained with 1,4-diphenylbutadiene as the substrate.
Synthesis of novel β-dialkylamino-α,β-unsaturated trifluoromethylketones containing cyclobutene fragment and their reactions with organolithium and Grignard reagents
Koldobskii, Andrey B.,Tsvetkov, Nikolai P.,Solodova, Ekaterina V.,Verteletskii, Pavel V.,Godovikov, Ivan A.,Kalinin, Valery N.
supporting information; experimental part, p. 3457 - 3462 (2010/06/21)
The highly reactive trifluoromethylenaminoketones, with a strained cyclobutene and norbornadiene moieties were firstly prepared from the corresponding β-halogeno-α,β-unsaturated trifluoromethylketones in almost quantitative yields. The ambident properties
Reaction of Perfluorinated Acetylenic Ketones with Cyclopentadienes
Zenova,Borisenko,Platonov,Proskurnina,Zefirov
, p. 951 - 954 (2007/10/03)
Cycloaddition of 1,1,1-trifluoro-4-phenyl-3-butyn-2-one to cyclopentadiene, spiro[2.4]hepta-4,6-diene, methylcyclopentadiene, and tert-butylcyclopentadiene has been studied.
