179996-42-0Relevant articles and documents
Silver-catalyzed formal [3+2]-cycloaddition of α-trifluoromethylated methyl isocyanides: a facile stereoselective synthesis of CF3-substituted heterocycles
Zhang, Xue,Wang, Xin,Gao, Yuelei,Xu, Xianxiu
supporting information, p. 2427 - 2430 (2017/03/01)
An Ag-catalyzed formal [3+2]-cycloaddition of α-trifluoromethylated methyl isocyanides with polar double bonds has been developed for the facile access to trifluoromethylated oxazolines, imidazolines and pyrrolines under mild conditions. The practicality of this chemistry is demonstrated by the gram-scale synthesis of oxazolines with excellent yields and facile transformations of the formed oxazolines to trifluoromethylated β-amino alcohols in quantitative yields.
BF3-promoted aromatic substitution of N-alkyl α-trifluoromethylated imine: Facile synthesis of 1-aryl-2,2,2-trifluoroethylamines
Gong, Yuefa,Kato, Katsuya,Kimoto, Hiroshi
, p. 2637 - 2645 (2007/10/03)
The aromatic substitution of three representative N-alkyl trifluoromethyl imines 1a-c (R: a, benzyl; b, benzhydryl; c, methyl), obtained from primary alkyl amines and trifluoroacetaldehyde ethyl hemiacetal, was used to investigate the preparation of 1-aryl-2,2,2-trifluoroethylamines. In the presence of BF3·OEt2, the reaction of imine 1 with various aromatic compounds proceeded smoothly at room temperature, giving N-alkyl-1-aryl-2,2,2-trifluoroethylamines in moderate-to-high yields. Moreover, successful regioselective removal of N-benzyl and N-benzhydryl groups was achieved by hydrolysis in hydrochloric acid or by palladium-catalyzed hydrogenolysis.
Mechanisms of decomposition of (Z)-2,2,2-trifluoro-1-arylethanediazoates in aqueous media
Finneman, Jari I.,Fishbein, James C.
, p. 7134 - 7138 (2007/10/03)
A study of the kinetics of decay of three (Z)-2,2,2-trifluoro-1-arylethanediazoates at 25°C in aqueous media, 4% 2-propanol by volume, ionic strength 1 M (NaClO4) in the pH range 4-13, as well as the results of experiments to detect deuterium incorporation into products from solvent is reported. It is concluded in the case of the unsubstituted compound that the buffer-independent reaction involves rate-limiting heterolytic bond fission of the diazoic acid to yield a diazonium ion intermediate, and a similar mechanism is indicated for the other two compounds. General acid catalysis of the decay of the diazoic acids at pH 7 is observed, and it is concluded that the reaction involves rate-limiting N-O bond cleavage of the diazoic acid that is concerted with protonation of the leaving hydroxide ion by the catalyst.