A Highly Stabilized Phosphonium Ylide that Forms Supramolecular Dimers in Solution and the Solid State
A Highly Stabilized Phosphonium Ylide that Forms Supramolecular Dimers in Solution and the Solid State
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DOI：
10.1002/chem.201904131
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发表时间：
2019-10-25
影响因子：
4.3
通讯作者：
Cao, Dennis D.
中科院分区：
文献类型：
--
作者：
Kim, Min Ji;Luo, Stella M.;Cao, Dennis D.
本工作描述了一个不寻常的鳞叶立德的形成时，试图合成的bisphosphonium均苯四酸二酰亚胺。光谱和晶体学表征表明，π-π和CHO相互作用的组合导致在溶液中和在固态的叶立德的超分子均二聚化。只有强酸才能质子化叶立德，否则它对维蒂希和烷基化反应是惰性的。总之，这些观察结果表明，该化合物是迄今为止发现的最高度稳定的鳞叶立德之一。
This work describes the unexpected formation of an unusual phosphonium ylide when attempting the synthesis of bisphosphonium pyromellitic diimides. Spectroscopic and crystallographic characterization reveals that a combination of pi-pi and CHO interactions leads to supramolecular homodimerization of the ylide both in solution and in the solid-state. Only strong acids are able to protonate the ylide, which is otherwise inert to Wittig and alkylation reactivity. Taken together, these observations indicate that this compound is one of the most highly stabilized phosphonium ylides discovered to date.