Add time:09/06/2019 Source:sciencedirect.com
Monoalkylations of different nucleophilic azoles were investigated with the electron-deficient trans-3,3,3-trifluoro-1-nitropropene (1) as alkylating reagent without addition of any catalyst. In each case, the bonding of the alkene at the azole occurs regioselectively at the trifluoromethyl-substituted C atom of the alkene, whereas the azoles react at different positions depending on the electron density of the heterocycles. Thus, 1-methyl-pyrrole (2) reacted with 1 under C-C bond formation giving the two regioisomers 2-(1-trifluoromethyl-2-nitroethyl)-1-methyl-pyrrole (3) (major product) and 3-(1-trifluoromethyl-2-nitroethyl)-1-methyl-pyrrole (4). The less nucleophilic pyrazole (5), 1,2,4-triazole (7), 3-bromo-1,2,4-triazole (9), and 3,5-dibromo-1,2,4-triazole (12) gave exclusively the corresponding N-alkyl azoles 1- (1-trifluoromethyl-2-nitroethyl )-pyrazole (6), 1-(1-trifluoromethyl-2-nitroethyl) -1,2,4-triazole (8), 3-bromo-1- (1-trifluoromethyl-2-nitroethyl)-1,2,4-triazole (10)/5-bromo-1-(1-trifluoromethyl-2-nitroethyl)-1,2,4-triazole (11), and 3,5-dibromo-1-(1-trifluoromethyl-2-nitroethyl)-1,2,4-triazole (13), respectively. The enantiomeric pairs of the chiral monoalkyl-azoles could not be separated. Moreover, we used trans-3,3,3-trifluoro-1-nitropropene (1) as a dienophile in Diels-Alder cycloadditions with cyclopentadiene (14), cyclohexa-1,3-diene (16), and furan (18). Two diastereomeric products (15A/15B, 17A/17B, and 19A/19B), which could not be separated by column chromatography, are formed from each diene. All compounds were characterized by 1H, 13C, and 19F NMR data.
We also recommend Trading Suppliers and Manufacturers of 5-bromo-1-methyl-1,2,4-triazole (cas 16681-72-4). Pls Click Website Link as below: cas 16681-72-4 suppliers
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View