- Copper-Catalyzed Ring-Opening 1,3-Aminotrifluoromethylation of Arylcyclopropanes
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The copper-catalyzed reaction of arylcyclopropanes, N-fluorobis(arenesulfonyl)imides, and (bpy)Zn(CF3)2 (bpy = 2,2′-bipyridine) at room temperature affords the corresponding ring-opening 1,3-aminotrifluoromethylation products in satisfactory yields. The protocol is highly regioselective, providing a convenient entry to γ-trifluoromethylated amines. A mechanism involving the trifluoromethylation of benzyl radicals is proposed.
- Zhang, Huan,Xiao, Haiwen,Jiang, Feng,Fang, Yewen,Zhu, Lin,Li, Chaozhong
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- A Novel Synthesis of N -Sulfonylformamidines from N Sulfonyl sulfonamides
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N -Sulfonylformamidines were synthesized from N -sulfonylsulfonamides by reacting with p -toluenesulfonyl chloride (TsCl) and N, N - disubstituted formamides. In this reaction, it was expected that mixing TsCl with the N, N -disubstituted formamide would generate an iminium salt (Vilsmeier reagent). The reaction avoids the use of metal catalysts and hazardous reagents, and the desired N -sulfonylformamidines were obtained in 60% to quantitative yields.
- Jeong, Yuri,Ban, Jaeyoung,Lim, Minkyung,Rhee, Hakjune
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supporting information
p. 1867 - 1874
(2018/02/26)
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- Effects of medium and substituents on dissociation of 4,4′-disubstituted bis(benzenesulfon)imides
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Ten 4,4′-disubstituted bis(arenesulfon)imides of the general formula XC6H4SO2NHSO2C6H 4X have been synthesized and their structures confirmed by their 1H NMR spectra. Elemental analyses are presented for the compounds not yet described. The dissociation constants of these model substances have been measured potentiometrically in pyridine, dimethylformamide, methanol, ethanol, propylene carbonate, acetone, acetonitrile, 1,2-dichloroethane and tetramethylene sulfone. The pKHA values obtained have been correlated with three sets of the Hammett substituent constants and the results have been used to discuss the solvent and substituent effects on the dissociation of the compounds studied. Sulfonimides with electron-acceptor substituents behave as rather strong acids in some solvents (pyridine, dimethylformamide, methanol and ethanol), whereas normal substituent dependences are found in other solvents. The experimental data have also been interpreted with the help of the statistical methods based on latent variables. From the calculations it follows that only the first principal component, which correlates well with the substituent constant sets adopted, is statistically significant in describing the substituent effect on the acid-base process studied.
- Ludwig, Miroslav,Stverka, Pavel
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p. 1205 - 1214
(2007/10/03)
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- New deaminations IX - pyrolysis of N-alkyl-N,N-disulfonimides
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N,N-Disulfonimide derivatives of certain alkyl amines stereoselectively pyrolyze without skeletal rearrangement to give up to 99% yields of alkenes.
- Curtis, Veronica A.,Knutson, Frank J.,Baumgarten, Ronald J.
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p. 199 - 202
(2007/10/02)
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