Stable Triazenes Derived from 2‐Alkylaminonaphthalenes and 5‐Nitrobenzo[<i>c</i>]‐1,2‐thiazole‐3‐diazonium Hydrogensulfate
作者:Josef Přikryl、Vladimír Macháček、Petr Jansa、Markéta Svobodová、Aleš Růžička、Petr Nachtigall、Michal Černý
DOI:10.1002/ejoc.200800180
日期:2008.7
confirmed that the extraordinary stability of the triazenes formed by an azo coupling reaction of 5-nitrobenzo[c]-1,2-thiazole-3-diazonium with primary or secondary aromatic amines is caused by the fact that these substances are protonated at the heterocyclic nitrogen atom and not at the nitrogen atom of the triazene grouping –N=N–N(R)Ar. Stable triazenes are also formed by reaction of 5-nitrobenzo[c]-1
使用 DFT 方法的计算证实,由 5-硝基苯并[c]-1,2-噻唑-3-重氮与芳香伯胺或仲胺的偶氮偶联反应形成的三氮烯具有非凡的稳定性,这是由于这些物质在杂环氮原子处质子化,而不是在三氮烯组 -N=N-N(R)Ar 的氮原子处质子化。5-硝基苯并[c]-1,2-噻唑-3-重氮与2-烷基氨基萘反应也可形成稳定的三氮烯。在与 2-甲氨基-和 2-乙氨基萘的偶氮偶联反应的情况下,三氮烯的含量在具有异构偶氮化合物的产物混合物中几乎为 50%。通过 X 射线分析证实了三氮烯的结构。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)