Photochemical synthesis of phosphinolines from phosphonium-iodonium ylides
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-r...
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| Hauptverfasser: | , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
2011
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| In: |
The journal of organic chemistry
Year: 2011, Jahrgang: 76, Heft: 2, Pages: 566-572 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/jo101993a |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/jo101993a
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| Verfasserangaben: | Elena D. Matveeva, Tatyana A. Podrugina, Marina A. Taranova, Anatolyi A. Borisenko, Andrey V. Mironov, Rolf Gleiter, Nikolay S. Zefirov |
| Zusammenfassung: | 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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| Beschreibung: | Published online: 22 December 2010 Gesehen am 12.08.2022 |
| Beschreibung: | Online Resource |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/jo101993a |