Regioselective and Stereoselective Addition of Tetrazole Derivatives to Electron-poor Acetylenic Esters in the Presence of Triphenylphosphine

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• 作者：Ali Ramazani ; Fatemeh Zeinali Nasrabadi ; Katarzyna Ślepokura ; Tadeusz Lis and Sang Woo Joo
• 刊名：Journal of Heterocyclic Chemistry
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：54
• 期：1
• 页码：55-64
• 全文大小：1948K
• ISSN：1943-5193

文摘

Protonation of the highly reactive 1:1 intermediates produced in the reaction between triphenylphosphine and acetylenic esters by tetrazole derivatives leads to the formation of vinyltriphenylphosphonium salts. The cation of these salts undergoes an addition reaction with the counter anion in CH₂Cl₂ at room temperature to yield the corresponding stabilized phosphorus ylides. Elimination of triphenylphosphine from the stabilized phosphorus ylides leads to the corresponding electron-poor N-vinyl tetrazoles in fairly high yields. Structures of N-vinyl tetrazoles were determined by IR, ¹H NMR, ¹³C NMR and single crystal X-ray structure analyses. The reaction is fairly regioselective and stereoselective.