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How electrophilic are 3-nitroindoles? Mechanistic investigations and application to a reagentless (4+2) cycloaddition
Chemical Communications ( IF 4.9 ) Pub Date : 2021-09-06 , DOI: 10.1039/d1cc04074j
Batoul Rkein 1 , Maxime Manneveau 1 , Ludovik Noël-Duchesneau 2 , Karine Pasturaud 1 , Muriel Durandetti 1 , Julien Legros 1 , Sami Lakhdar 2, 3 , Isabelle Chataigner 1, 4
Affiliation  

The electrophilicity of 4 different 3-nitroindole derivatives has been evaluated by Mayr’s linear free energy relationship (log k(20 °C) = sN(E + N)) and reveals unexpected values for aromatic compounds, in the nitrostyrene range. 3-Nitroindoles are sufficiently electrophilic to interact with a common diene namely the Danishefsky's diene at room temperature, in the absence of any activator, to furnish smoothly the dearomatized (4+2) cycloadducts in good yields.

中文翻译:

3-硝基吲哚的亲电性如何?无试剂(4+2)环加成的机理研究和应用

4 种不同的 3-硝基吲哚衍生物的亲电性已通过 Mayr 的线性自由能关系(log k (20 °C) = s N ( E + N ))进行评估, 并揭示了芳族化合物在硝基苯乙烯范围内的意外值。在没有任何活化剂的情况下,3-硝基吲哚具有足够的亲电子性,可以在室温下与常见的二烯(即丹麦谢夫斯基二烯)相互作用,以良好的产率顺利提供脱芳构化的 (4+2) 环加合物。
更新日期:2021-09-13
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