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ylide main text 3July2019.pdf (1.31 MB)

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

submitted on 03.07.2019, 20:11 and posted on 05.07.2019, 15:42 by Min Ji Kim, Stella Luo, Andrew Greenlee, Victor Young, Jr., Dennis Cao
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.


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American Chemical Society Petroleum Research Fund 57163-UNI1


Email Address of Submitting Author


Macalester College


United States

ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest

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Version to be submitted for peer review