A Highly Stabilized Phosphonium Ylide That Forms Supramolecular Dimers in Solution and Solid State

05 July 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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 π-π and CH•••O 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.


Ylide Formation
aromatic diimides
pyromellitic diimide


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