Phosphorus 3‐membered heterocycles, phosphiranes, provide an interesting synthetic scaffold with a potentially diverse range of reactions that are currently underexplored. This is in part due to their difficulty in synthesis, with many products and intermediates containing low air stability. With the application and extension of a density functional theory (DFT) model to phosphiranes by calculation at the UB3LYP/6‐31G(d) level of their radical cation singly occupied molecular orbital (SOMO), a correlation between calculated and relative experimental air stability has been demonstrated. The model also accounts for the stability of many synthesised substituted and unsubstituted phosphiranes and has allowed new synthetic targets to be identified, in particular, 1‐(2,4,6‐tri‐tert‐butoxyphenyl)phosphirane exhibited high theoretical air stability. Because of the simplicity and efficiency of the model, its application enables phosphiranes to be screened for high bench stability, providing accessibility for their use in synthetic chemistry, in turn, realising the potential for incorporation of phosphiranes into complex synthetic strategies.

中文翻译：

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利用密度泛函理论预测膦烷的空气稳定性

磷3元杂环，膦腈，提供了一种有趣的合成支架，具有目前尚未充分开发的各种潜在反应。部分原因是由于它们的合成困难，许多产品和中间体的空气稳定性差。随着密度泛函理论（DFT）模型的应用和扩展，通过在其自由基阳离子单占据分子轨道（SOMO）的UB3LYP / 6-31G（d）水平上的计算，对膦进行了计算，相对于实验空气稳定性之间存在相关性已经证明。该模型还考虑了许多合成的取代和未取代的膦酮的稳定性，并允许确定新的合成目标，特别是1-（2,4,6-三叔丁氧基苯基）膦烷具有较高的理论空气稳定性。