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

preprint
submitted on 03.07.2019 and posted on 05.07.2019 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.

Funding

MRI: Acquisition of a Computer Cluster for Undergraduate Chemistry Research and Teaching by the Midwest Undergraduate Computational Chemistry Consortium (MU3C)

Directorate for Mathematical & Physical Sciences

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MRI: Acquisition of a single-crystal diffractometer for the University of Minnesota

Directorate for Mathematical & Physical Sciences

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NNCI: Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource

Directorate for Engineering

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American Chemical Society Petroleum Research Fund 57163-UNI1

History

Email Address of Submitting Author

dcao@macalester.edu

Institution

Macalester College

Country

United States

ORCID For Submitting Author

0000-0002-0315-1619

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version to be submitted for peer review

Exports