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Synthesis 2022; 54(07): 1745-1752
DOI: 10.1055/s-0037-1610788
DOI: 10.1055/s-0037-1610788
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Quaternary Phosphonium Carboxylates: Structure, Dynamics and Intriguing Olefination Mechanism
Abstract
We have earlier shown how the Wittig chemistry can be done using novel Eigenbase phosphonium carboxylate reagents. Here we discuss the phenomenon of ion pairing, their solution tautomerism, solid-state structure, and mechanistic aspects of olefination. The results point to a complex process involving unfamiliar H-bond-driven ion-pair equilibria followed by standard Wittig reaction steps.
Key words
quaternary phosphonium salts - ion pairs - Wittig reaction - proton-transfer equilibrium - fluxional behaviourSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610788.
- Supporting Information
Publication History
Received: 09 August 2021
Accepted after revision: 05 November 2021
Article published online:
21 December 2021
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Kinetics techniques lead to lower pK a values: