133640-88-7Relevant articles and documents
Selectivity of (Trifluoromethyl)chlorocarbene
Moss, Robert A.,Guo, Wenjeng,Denney, Dorothy Z.,Houk, K. N.,Rondan, Nelson G.
, p. 6164 - 6169 (1981)
(Trifluoromethyl)chlorocarbene (CF3CCl) was generated by photolysis of 3-(trifluoromethyl)-3-chlorodiazirine and added to eight alkenes affording the corresponding cyclopropanes.Additions to cis- and trans-butenes were stereospecific.No allylic CH insertion products were observed with any of the substrates.Substrates, reactivities (relative to Me2C=CH2) = 1.00, and stereoselectivities (syn-Cl/anti-Cl) for the CF3CCl addition reactions follow: Me2C=CMe2, 0.92, none; Me2C=CHMe, 1.17, 1.48; Me2C=CH2, 1.00, none; cis-MeCH=CHMe, 0.88, 1.65; trans-MeCH=CHMe, 0.62, none; EtCH=CH2, 0.48, 1.28; i-PrCH=CH2, 0.25, 1.36; t-BuCH=CH2, 0.11, 1.66.The reactivity data are analyzed and compared to analogous results for CH3CCl and CCl2.The carbene selectivity index, mCXY, of CF3CCl is ca. 0.19 (mCCl2 = 1.00), and its steric demand during addition to RCH=CH2 (Taft δ) is 0.41 (δCCl2 = 0.88).Relative to CH3CCl, CF3 strongly destabilizes CF3CCl.This conclusion follows both from analysis of the experimental data and from ab initio calculations.CF3CCl is believed to add to alkenes via "early", relatively "open" transition states, in which electronic and steric selectivities are leveled.
2-Trifluoromethyl-1,3-diazabutadienes as useful intermediates for the construction of 2-trifluoromethylpyrimidine derivatives
Medina-Mercado, Ignacio,Zaragoza-Galicia, Ivann,Olivo, Horacio F.,Romero-Ortega, Moisés
, p. 4133 - 4139 (2018/10/19)
A methodology to prepare 2-trifluoromethylpyrimidines has been developed on the basis of a cyclization reaction of 2-trifluoromethyl-1,3-diazabutadienes. These 2-trifluoromethyl-1,3-diazabutadienes were prepared by the condensation of trifluoroacetamidine and amide acetals or with chloromethaniminium salt derived from N, N-dimethylbenzamide with phosphorus oxychloride. The cycloaddition reactions of these 2-trifluoromethyl-1,3-diazabutadienes with DMAD and phenylacetyl chloride provided 2-trifluoromethylpyrimidine derivatives in regular to moderate overall yield.
2-trifluoromethylpyrimidin-4-carboxylic acid and its derivatives and preparation method thereof
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Paragraph 0035; 0036, (2017/05/23)
The invention relates to 2-trifluoromethylpyrimidin-4-carboxylic acid with a general formula (I) and its derivatives. In the general formula (I), R represents COOH, COOX, COORn, COOCH3, COOCH2CH3 or CH2OH, X represents any alkali or amine which can react with a strong acid or carboxylic acid to produce a salt and Rn represents any carbonyl compound. The invention also relates to a preparation method of the compound. The preparation method has good controllability, mainly solves the technical problem of large-scale production limitation and has a good application prospect.