Terminal bis-acetylenes derived from 1,2-bis(1H-tetrazol-5-yl)ethane

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• 作者：R. I. Ishmetova ; D. S. Yachevskii ; N. K. Ignatenko…
• 关键词：Key words1 ; 2 ; bis(1H ; tetrazol ; 5 ; yl)ethane ; alkylation ; propargyl bromide ; terminal bis ; acetylenes ; 1 ; 2 ; bis[1 ; (prop ; 2 ; yn ; 1 ; yl) ; 1H ; tetrazol ; 5 ; yl]ethane ; p ; tolyl azide ; p ; nitrophenyl azide ; benzyl azide ; poly(glycidyl azide) ; [3+2] cycloaddition ; X ; ray diffraction analysis
• 刊名：Russian Chemical Bulletin
• 出版年：2016
• 出版时间：May 2016
• 年：2016
• 卷：65
• 期：5
• 页码：1268-1271
• 全文大小：
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry;
• 出版者：Springer US
• ISSN：1573-9171
• 卷排序：65

文摘

The N(1)—N(1), N(2)—N(2), and N(1)—N(2) regioisomers of 1,2-bis[(prop-2-yn-1-yl)-1H-tetrazol-5-yl]ethane were first synthesized by alkylation of 1,2-bis(1H-tetrazol-5-yl)ethane with propargyl bromide. The peculiarities of the crystal structure of 1,2-bis[1-(prop-2-yn-1-yl)-1H-tetrazol-5-yl]ethane were evaluated by X-ray diffraction analysis. This compound is readily underwent Cu-catalyzed [3+2] cycloaddition with p-tolyl azide, p-nitrophenyl azide, and benzyl azide to give heterocyclic assembles bearing 1,2,3-triazole and tetrazole cycles. Catalyst-free [3+2] cycloadditions of 1,2-bis[1-(prop-2-yn-1-yl)-1H-tetrazol-5-yl]ethane and the mixtures of the N(1)—N(1), N(2)—N(2), N(1)—N(2) regioisomers with poly(glycidyl azide) oligomers resulted in 1,2,3-triazole cycles and crosslinking of the polymer chains.