A General Strategy for Increasing the Air Stability of Phosphines Including Primary Phosphines
| dc.date.accessioned | 2024-02-07T13:31:11Z | |
| dc.date.available | 2024-02-07T13:31:11Z | |
| dc.date.issued | 2023-08-31 | |
| dc.identifier | doi:10.17170/kobra-202312129213 | |
| dc.identifier.uri | http://hdl.handle.net/123456789/15442 | |
| dc.description.sponsorship | Gefördert im Rahmen des Projekts DEAL | ger |
| dc.description.sponsorship | Deutsche Forschungsgemeinschaft; Hessisches Ministerium für Wissenschaft und Kunst | ger |
| dc.language.iso | eng | |
| dc.rights | Namensnennung 4.0 International | * |
| dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | * |
| dc.subject | autoxidation | eng |
| dc.subject | primary phosphines | eng |
| dc.subject | primary phosphine oxides | eng |
| dc.subject | singlet oxygen quenching | eng |
| dc.subject.ddc | 540 | |
| dc.title | A General Strategy for Increasing the Air Stability of Phosphines Including Primary Phosphines | eng |
| dc.type | Aufsatz | |
| dcterms.abstract | A general approach for increasing the air-stability of various primary phosphines in the absence of kinetic stabilization is presented that contrasts with previous interpretations, which were limited to specific phosphines. This contribution shows the synthesis of a series of air-stable primary phosphines Fc(CH₂)nPH₂, where n=0,1,2,3; and Fc=ferrocenyl, and their corresponding isolable primary phosphine oxides. It was demonstrated that the ferrocene moiety exerts an antioxidant effect on the primary phosphine group, which is intermolecular, solvent dependent and increases with the electron density on the ferrocene moiety. Furthermore, we demonstrated that the presence of ferrocene in solution also inhibits the oxidation of other secondary and tertiary phosphines in air. Together our findings suggest that quenching of singlet oxygen is the actual reason for the antioxidant effect; this was experimentally confirmed by using other established singlet oxygen quenchers, thus demonstrating a key role of singlet oxygen in the aerobic oxidation of phosphines. | eng |
| dcterms.accessRights | open access | |
| dcterms.creator | Horký, Filip | |
| dcterms.creator | Franz, Roman | |
| dcterms.creator | Bruhn, Clemens | |
| dcterms.creator | Pietschnig, Rudolf | |
| dc.relation.doi | doi:10.1002/chem.202302518 | |
| dc.relation.projectid | Grant Number: HO7221/1-1; Grant Number: LOEWE SMolBits | |
| dc.subject.swd | Autoxidation | ger |
| dc.subject.swd | Phosphine | ger |
| dc.subject.swd | Sauerstoff | ger |
| dc.subject.swd | Chemische Eigenschaft | ger |
| dc.type.version | publishedVersion | |
| dcterms.source.identifier | eissn:1521-3765 | |
| dcterms.source.issue | Issue 68 | |
| dcterms.source.journal | Chemistry – A European Journal | eng |
| dcterms.source.volume | Volume 29 | |
| kup.iskup | false | |
| dcterms.source.articlenumber | e202302518 |
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