Date
2024-03-30Metadata
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Aufsatz
Synthesis, structure, and stability of a set of C-stereogenic heteroditopic P, S ligands☆
Abstract
This study focuses on synthesis and investigation of coordination modes of phosphorus and sulfur-containing C-stereogenic compounds, prepared from thioanisole. Isolation of the C-stereogenic organolithium compound [RR'CHLi2THF]₂ (R = C₆H₅S, R’ = (CH₃)₃Si, THF = tetrahydrofuran) instead of in situ usage turned out to be mandatory for controlled reactivity. Variation of the steric and electronic properties of the substituents at phosphorus furnished three different phosphane substituted P, S ligands RR'CHPPh₂, RR'CHP(N(C₂H₅)₂)₂, and RR'CHP(t-C₄H₉)₂. Furthermore, the corresponding chalcogenphosphoranes were synthesized by oxidation with elemental sulfur and selenium. Preliminary investigation of the coordination behavior of RR'CHP(t-C₄H₉)₂, RR'CHP(S)(t-C₄H₉)₂ and RR'CHP(Se)(t-C₄H₉)₂ towards coinage metals was explored with Au(tht)Cl, both for the phosphanes and the corresponding phosphoranes. Intermolecular aurophilic interactions have been observed for the selenophosphorane exclusively.
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Gefördert im Rahmen des Projekts DEALCitation
@article{doi:10.17170/kobra-2024080710643,
author={Mammadova, Aynura and Kargin, Denis and Bruhn, Clemens and Pietschnig, Rudolf},
title={Synthesis, structure, and stability of a set of C-stereogenic heteroditopic P, S ligands☆},
journal={Journal of Organometallic Chemistry},
year={2024}
}
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0501 Text $btxt$2rdacontent
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3000 Mammadova, Aynura
3010 Kargin, Denis
3010 Bruhn, Clemens
3010 Pietschnig, Rudolf
4000 Synthesis, structure, and stability of a set of C-stereogenic heteroditopic P, S ligands☆ / Mammadova, Aynura
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5550 {{Phosphor}}
5550 {{Schwefel}}
5550 {{Komplexbildungsreaktion}}
5550 {{Goldkomplexe}}
5550 {{Lithiumorganische Verbindungen}}
5550 {{Chiralität <Chemie>}}
7136 ##0##http://hdl.handle.net/123456789/15959
<resource xsi:schemaLocation="http://datacite.org/schema/kernel-2.2 http://schema.datacite.org/meta/kernel-2.2/metadata.xsd"> 2024-08-07T14:12:05Z 2024-08-07T14:12:05Z 2024-03-30 doi:10.17170/kobra-2024080710643 http://hdl.handle.net/123456789/15959 Gefördert im Rahmen des Projekts DEAL eng Namensnennung 4.0 International http://creativecommons.org/licenses/by/4.0/ Phosphorus Sulfur Gold (I) complexation Organolithium Heteronuclear NMR Chirality 540 Synthesis, structure, and stability of a set of C-stereogenic heteroditopic P, S ligands☆ Aufsatz This study focuses on synthesis and investigation of coordination modes of phosphorus and sulfur-containing C-stereogenic compounds, prepared from thioanisole. Isolation of the C-stereogenic organolithium compound [RR'CHLi2THF]₂ (R = C₆H₅S, R’ = (CH₃)₃Si, THF = tetrahydrofuran) instead of in situ usage turned out to be mandatory for controlled reactivity. Variation of the steric and electronic properties of the substituents at phosphorus furnished three different phosphane substituted P, S ligands RR'CHPPh₂, RR'CHP(N(C₂H₅)₂)₂, and RR'CHP(t-C₄H₉)₂. Furthermore, the corresponding chalcogenphosphoranes were synthesized by oxidation with elemental sulfur and selenium. Preliminary investigation of the coordination behavior of RR'CHP(t-C₄H₉)₂, RR'CHP(S)(t-C₄H₉)₂ and RR'CHP(Se)(t-C₄H₉)₂ towards coinage metals was explored with Au(tht)Cl, both for the phosphanes and the corresponding phosphoranes. Intermolecular aurophilic interactions have been observed for the selenophosphorane exclusively. open access Mammadova, Aynura Kargin, Denis Bruhn, Clemens Pietschnig, Rudolf 9 Seiten doi:10.1016/j.jorganchem.2024.123113 Phosphor Schwefel Komplexbildungsreaktion Goldkomplexe Lithiumorganische Verbindungen Chiralität <Chemie> publishedVersion eissn:1872-8561 Issue May Journal of Organometallic Chemistry Volume 1011 false 123113 </resource>
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