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Furyl-substituted mixed phosphonium-iodonium ylides in the synthesis of annelated P-containing heterocyclic compounds

Abstract Photochemical reactions between stabilized furyl-substituted phosphonium?iodonium ylides and terminal acetylenes led to the formation of new P-containing heterocyclic compounds. For the heterocyclization of 2-furyl-substituted ylides, we observed an unprecedented electrophilic ipso attack o...

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Main Authors: Matveeva, Elena D. (Author) , Vinogradov, Dmitrii S. (Author) , Podrugina, Tatyana A. (Author) , Nekipelova, Tatiana D. (Author) , Mironov, Andrey V. (Author) , Gleiter, Rolf (Author) , Zefirov, Nikolay S. (Author)
Format: Article (Journal)
Language:English
Published: October 21, 2015
In: European journal of organic chemistry
Year: 2015, Issue: 33, Pages: 7324-7333
ISSN:1099-0690
DOI:10.1002/ejoc.201500876
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.201500876
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201500876
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Author Notes:Elena D. Matveeva, Dmitrii S. Vinogradov, Tatyana A. Podrugina, Tatiana D. Nekipelova, Andrey V. Mironov, Rolf Gleiter, and Nikolay S. Zefirov
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Summary:Abstract Photochemical reactions between stabilized furyl-substituted phosphonium?iodonium ylides and terminal acetylenes led to the formation of new P-containing heterocyclic compounds. For the heterocyclization of 2-furyl-substituted ylides, we observed an unprecedented electrophilic ipso attack onto the α position of the furan ring in a carbocationic intermediate, leading ? via a spiro intermediate ? to the rearranged product with a 2,3-shift in the furan ring.
Item Description:Gesehen am 09.06.2020
Physical Description:Online Resource
ISSN:1099-0690
DOI:10.1002/ejoc.201500876

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