Although azomethine ylides have been fully exploited as versatile reactive intermediates in dipolar cycloaddition reactions to construct a variety of heterocyclic compounds involving a nitrogen atom, little is known about their structural and electronic properties. Here a method is developed for the preparation, isolation and characterization of a stable 2-azaphenalenyl based azomethine ylide. N-Phenyl-5,8-di-t-butyl-2-azaphenalenyl cannot be isolated because it undergoes rapid dimerization by C–C bond formation at the 1 and 3 positions. In contrast, sterically bulkier N-2,6-di(isopropyl)phenyl-5,8-di-t-butyl-2-azaphenalenyl can be generated and isolated as deep green crystals under deoxygenated conditions. X-ray crystal analysis of this stable azomethine ylide reveals that its azaphenalenyl skeleton has very small bond alternation and structural deformation. The results of spectroscopic and electrochemical theoretical studies indicate that N-2,6-di(isopropyl)phenyl-5,8-di-t-butyl-2-azaphenalenyl has electronic features that are similar to those of phenalenyl anion and it possesses an extremely high HOMO energy.

尽管在二极环加成反应中偶氮甲碱已被充分用作通用的反应性中间体，以构建各种涉及氮原子的杂环化合物，但对其结构和电子性质知之甚少。在此开发了一种用于制备，分离和表征稳定的基于2-氮杂烯基的偶氮甲碱叶立德的方法。ñ -苯基-5,8-二-吨-丁基-2- azaphenalenyl不能分离，因为它通过在1个3位的C-C键形成经历快速二聚化。相反，空间上较大的N -2,6-二（异丙基）苯基-5,8-二-t可以在脱氧条件下生成并分离出深绿色晶体状的丁基-2-氮杂苯并烯基。对这种稳定的甲亚胺叶立德的X射线晶体分析表明，其氮杂苯烯基骨架具有非常小的键交替和结构变形。光谱和电化学理论研究的结果表明，Ñ -2,6-二（异丙基）苯基-5,8-二-吨-丁基-2- azaphenalenyl具有电子的功能，类似于非那烯基阴离子，它具有一个极高的HOMO能量。