Versatile New Reagent for Nitrosation under Mild Conditions,Organic Letters

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Versatile New Reagent for Nitrosation under Mild Conditions
Organic Letters ( IF 4.9 ) Pub Date : 2021-04-12 , DOI: 10.1021/acs.orglett.1c00637
Jordan D Galloway ₁ , Cristian Sarabia ₁ , James C Fettinger ₂ , Hrant P Hratchian ₁ , Ryan D Baxter ₁

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Here we report a new chemical reagent for transnitrosation under mild experimental conditions. This new reagent is stable to air and moisture across a broad range of temperatures and is effective for transnitrosation in multiple solvents. Compared with traditional nitrosation methods, our reagent shows high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. Several challenging nitroso compounds are accessed here for the first time, including ¹⁵N isotopologues. X-ray data confirm that two rotational isomers of the reagent are configurationally stable at room temperature, although only one isomer is effective for transnitrosation. Computational analysis describes the energetics of rotamer interconversion, including interesting geometry-dependent hybridization effects.

中文翻译：

温和条件下用于亚硝化的多功能新试剂

在这里，我们报告了一种在温和的实验条件下进行反硝化的新化学试剂。这种新试剂在很宽的温度范围内对空气和湿气都稳定，并且对多种溶剂中的亚硝基化有效。与传统的亚硝化方法相比，我们的试剂对易氧化或可逆转亚硝化的底物显示出较高的官能团耐受性。首次在此访问了几种具有挑战性的亚硝基化合物，其中包括^15种N个同位素。X射线数据证实了该试剂的两种旋转异构体在室温下是构型稳定的，尽管仅一种异构体对亚硝基化有效。计算分析描述了旋转异构体相互转化的能量，包括有趣的几何依赖性杂交效应。

更新日期：2021-05-07

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