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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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Main Authors: Matveeva, Elena D. (Author) , Podrugina, Tatyana A. (Author) , Taranova, Marina A. (Author) , Borisenko, Anatolyi A. (Author) , Mironov, Andrey V. (Author) , Gleiter, Rolf (Author) , Zefirov, Nikolay S. (Author)
Format: Article (Journal)
Language:English
Published: 2011
In: The journal of organic chemistry
Year: 2011, Volume: 76, Issue: 2, Pages: 566-572
ISSN:1520-6904
DOI:10.1021/jo101993a
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/jo101993a
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Author Notes:Elena D. Matveeva, Tatyana A. Podrugina, Marina A. Taranova, Anatolyi A. Borisenko, Andrey V. Mironov, Rolf Gleiter, Nikolay S. Zefirov
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Summary: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.
Item Description:Published online: 22 December 2010
Gesehen am 12.08.2022
Physical Description:Online Resource
ISSN:1520-6904
DOI:10.1021/jo101993a

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