In the past, the use of nitrogen ylides focused primarily on cycloadditions, where the 1,3‐dipole was used as a building block for the formation of heterocycles such as pyrroles or pyrrolinones. In this work, we present a new perspective on imidazolium dicyanomethylides with their synthesis and utilization as anionic N‐heterocyclic carbenes (NHCs). The values of relative carbene formation energies (CREF) for a wide range of substituted imidazolium ylides unknown in the literature showed promising properties. In situ trapping reactions of these anionic NHCs with selenium led to anionic, water‐soluble compounds that exhibited remarkable coordination behavior according to X‐ray structure analyses. In addition, the 77Se shifts of the investigated compounds were measured to draw conclusions about their π‐acceptance.

中文翻译：

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咪唑鎓二氰基甲基化物作为阴离子 N-杂环卡宾的 N-叶立德前体

过去，氮叶立德的使用主要集中在环加成上，其中 1,3-偶极子被用作形成吡咯或吡咯啉酮等杂环的结构单元。在这项工作中，我们提出了咪唑二氰基甲基化物及其作为阴离子N-杂环卡宾（NHC）的合成和利用的新视角。文献中未知的各种取代咪唑鎓叶立德的相对卡宾形成能（CREF）值显示出有前景的特性。这些阴离子 NHC 与硒的原位捕获反应产生阴离子水溶性化合物，根据 X 射线结构分析，这些化合物表现出显着的配位行为。除此之外77测量所研究化合物的 Se 位移，得出有关其 π 接受的结论。