Nitrenes are a highly reactive, yet fundamental compound class. They possess a mono-valent nitrogen atom and usually a short life span, typically in the nanosecond range. Here, we report on the synthesis of a stable nitrene by photolysis of the arylazide M S FluindN 3 ( 1 ), which gave rise to the quantitative formation of the arylnitrene M S FluindN ( 2 ) (M S Fluind = dispiro[fluorene-9,3′-(1’,1’,7’,7’-tetramethyl-s-hydrindacen-4’-yl)-5′,9’’-fluorene]), that remains unchanged for at least 3 days when stored under argon atmosphere at room temperature. The extraordinary life span permitted the full characterization of 2 by single crystal x-ray crystallography, EPR spectroscopy and SQUID magnetometry, which supported a triplet ground state. Theoretical simulations suggest in addition to the kinetic stabilization conferred by the bulky M S Fluind aryl substituent, that electron delocalization across the central aromatic ring contributes to the electron stabilization of 2 .

中文翻译：

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稳定结晶氮烯的合成


氮烯是一种高反应性但基本的化合物类别。它们拥有一价氮原子，寿命通常很短，通常在纳秒范围内。在这里，我们报道了通过光解芳基叠氮化物 MS FluindN 3 ( 1 ) 合成稳定的氮烯，从而定量形成芳基氮烯 MS FluindN ( 2 ) (MS Fluind = 二螺[芴-9,3′ -(1',1',7',7'-四甲基-s-茚-4'-基)-5',9''-芴])，在氩气气氛下储存至少3天保持不变在室温下。非凡的寿命使得 2 能够通过单晶 X 射线晶体学、EPR 光谱和 SQUID 磁力测定法进行全面表征，支持三线态基态。理论模拟表明，除了庞大的 MS Fluind 芳基取代基赋予的动力学稳定性之外，中心芳环上的电子离域也有助于 2 的电子稳定性。