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| Verfasst von: | Matveeva, Elena D. [VerfasserIn]  |
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| | Podrugina, Tatyana A. [VerfasserIn] |
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| | Taranova, Marina A. [VerfasserIn] |
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| | Borisenko, Anatolyi A. [VerfasserIn] |
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| | Mironov, Andrey V. [VerfasserIn] |
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| | Gleiter, Rolf [VerfasserIn] |
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| | Zefirov, Nikolay S. [VerfasserIn] |
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| Titel: | Photochemical synthesis of phosphinolines from phosphonium-iodonium ylides |
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| Verf.angabe: | Elena D. Matveeva, Tatyana A. Podrugina, Marina A. Taranova, Anatolyi A. Borisenko, Andrey V. Mironov, Rolf Gleiter, Nikolay S. Zefirov |
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| Jahr: | 2011 |
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| Umfang: | 7 S. |
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| Fussnoten: | Published online: 22 December 2010 ; Gesehen am 12.08.2022 |
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| Titel Quelle: | Enthalten in: The journal of organic chemistry |
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| Ort Quelle: | [S.l.] : American Chemical Society, 1936 |
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| Jahr Quelle: | 2011 |
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| Band/Heft Quelle: | 76(2011), 2, Seite 566-572 |
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| ISSN Quelle: | 1520-6904 |
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| Abstract: | We describe three different series of experiments which were undertaken to test our hypothesis that during irradiation of phosphonium−iodonium ylides (1a, 1b) an electrophilic carbene is generated. By opposing the assumed intermediate to monosubstituted alkynes, we observed in the case of electron-rich substituents at the triple bond a domination of a 1,3-dipolar cycloaddition of the intermediate with the triple bond to yield furans. In the case of electron poorer substituents, the formation of phosphinolines prevails. A second series of experiments was carried out with mixed ylides in which one phenyl ring at the triarylphosphonium group was replaced by a thienyl group. In this case, we observe only an intramolecular reaction with the thienyl ring to yield the phosphinolines 21−23. In a third test, we replaced in the mixed ylides 1a, 1b the COR group by a CN substituent. This modification leads to phosphinolines only and avoids a 1,3-dipolar cycloaddition. |
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| DOI: | doi:10.1021/jo101993a |
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| URL: | Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.
Volltext: https://doi.org/10.1021/jo101993a |
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| | DOI: https://doi.org/10.1021/jo101993a |
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| Datenträger: | Online-Ressource |
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| Sprache: | eng |
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| K10plus-PPN: | 1814228411 |
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| Verknüpfungen: | → Zeitschrift |
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Photochemical synthesis of phosphinolines from phosphonium-iodonium ylides / Matveeva, Elena D. [VerfasserIn]; 2011 (Online-Ressource)
