文献类型：期刊文献

英文题名：Synthesis of 1-(substituted benzyl)-1,2,3-triazoles by 1,3-dipolar cycloaddition reaction

作者：Hu, YH; Liu, SL; Tong, QY; Huang, FR; Shen, YJ; Qi, HM; Du, L

机构：[1]E China Univ Sci & Technol, Sch Mat Sci & Engn, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2004

卷号：24

期号：10

起止页码：1228

外文期刊名：CHINESE JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000224369300010)】；

语种：英文

外文关键词：azide; phenylacetylene; 1,2,3-triazole; 1,3-dipolar cycloaddition reaction

摘要：Benzyl azide, 4-methyl-benzyl azide, 4-cyano-benzyl azide, 4-fluoro-benzyl azide and 1,1'-biazidomethyl-4,4'-biphenyl were prepared by the nucleophilic substitution reaction of NaN3 with substituted benzyl chlorides. The reaction rate was affected by the substitution groups at the phenyl ring, and electron-withdrawing groups could accelerate the rate. And 1,3-dipolar cycloaddition reaction of the azides with phenylacetylene was studied. The corresponding compounds (azides and 1,2,3-triazoles) were characterized with NMR, FT-IR and elementary analysis. The 1,2,3-triazoles were thermal stable. The addition rate depended on the substitution groups of the azides (1,3-dipole), and the reactivities correlated with polar effects: phenyacetylene (dipolarophile) reacted faster with electron-poor azides and vice versa. The 1, 3-dipolar cycloaddition reaction was found to be regioselective, and the 4-phenyl-1,2,3-triazoles were the major products in the two structural isomers of 1,2,3-triazoles obtained.