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Steric and Electronic Effects on Thermal Stability of Nitrile N-Oxide: a Case Study of Naphthalen-2-ol Derived Substrates
Chemistry Letters ( IF 1.6 ) Pub Date : 2021-09-09 , DOI: 10.1246/cl.210427
Shiho Bando 1 , Souma Ooba 1 , Kaori Miura 2 , Noriyuki Nakajima 1, 3 , Masahiro Hamada 1, 3 , Toshikazu Takata 2, 4 , Yasuhito Koyama 1, 3
Affiliation  

This paper describes the syntheses of four types of nitrile N-oxides (NOs) and the studies on the thermal isomerization of NOs to isocyanates (Isocs). It is found that a bulky electron-withdrawing substituent at the ortho position of NO tends to suppress the thermal degradation of NO. The reaction rates for the thermal reactions appear to be dependent on the initial concentration. The reaction orders are analyzed in order to understand the reaction mechanism for the isomerization. It is indicated that the isomerization of NO could proceed via a reversible formation of polymeric intermediate.

中文翻译:

腈氮氧化物热稳定性的空间和电子效应:Naphthalen-2-ol 衍生基材的案例研究

本文描述了四种类型的腈的合成Ñ -oxides(NO或多个),而位于该热异构化研究NO异氰酸酯(S ISOC多个)。据发现,在一个大体积的吸电子取代基的邻位的位置NO趋向于抑制热降解NO。热反应的反应速率似乎取决于初始浓度。分析反应顺序以了解异构化的反应机理。表明NO的异构化可以通过聚合中间体的可逆形成进行。
更新日期:2021-09-09
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