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Generation of boryl-nitroxide radicals from a boraalkene via the nitroso ene reaction
Chemical Science ( IF 7.6 ) Pub Date : 2022-08-18 , DOI: 10.1039/d2sc02485c Chaohuang Chen 1 , Constantin G Daniliuc 1 , Sina Klabunde 2 , Michael Ryan Hansen 2 , Gerald Kehr 1 , Gerhard Erker 1
Chemical Science ( IF 7.6 ) Pub Date : 2022-08-18 , DOI: 10.1039/d2sc02485c Chaohuang Chen 1 , Constantin G Daniliuc 1 , Sina Klabunde 2 , Michael Ryan Hansen 2 , Gerald Kehr 1 , Gerhard Erker 1
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Examples of isolated boron substituted nitroxide radicals are rare. The reaction of the reactive cyclic boraalkene 3 with nitrosobenzene yields a mixture of the [2 + 2] cycloaddition product 4a, the B-nitroxide radicals 5a and 6a and the azoxybenzene co-product 7a via a bora nitroso ene reaction pathway, the boron analogue of the nitroso ene reaction. The products were separated by flash chromatography, and the B-nitroxide radicals were characterized by X-ray diffraction and EPR spectroscopy. Radical 5a was shown to be a hydrogen atom abstractor. Both the B-nitroxide radicals are more easily oxidized compared to e.g. TEMPO, as shown by cyclic voltammetry.
中文翻译：
通过亚硝基烯反应从硼烷生成硼基-硝基氧自由基
孤立的硼取代的氮氧自由基的例子很少见。反应性环状硼烯3与亚硝基苯的反应产生 [2 + 2] 环加成产物4a、B-硝基氧自由基5a和6a以及偶氮基苯副产物7a 通过硼亚硝基苯反应途径的混合物，硼类似物亚硝基烯反应。通过快速色谱分离产物，并通过X射线衍射和EPR光谱表征B-硝基氧自由基。自由基5a被证明是一个氢原子吸收剂。两个B与例如TEMPO相比，-氮氧自由基更容易被氧化，如循环伏安法所示。
更新日期：2022-08-18
中文翻译：
通过亚硝基烯反应从硼烷生成硼基-硝基氧自由基
孤立的硼取代的氮氧自由基的例子很少见。反应性环状硼烯3与亚硝基苯的反应产生 [2 + 2] 环加成产物4a、B-硝基氧自由基5a和6a以及偶氮基苯副产物7a 通过硼亚硝基苯反应途径的混合物，硼类似物亚硝基烯反应。通过快速色谱分离产物，并通过X射线衍射和EPR光谱表征B-硝基氧自由基。自由基5a被证明是一个氢原子吸收剂。两个B与例如TEMPO相比，-氮氧自由基更容易被氧化，如循环伏安法所示。
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