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  New reaction of ethenetetracarbonitrile with N-arylisoindolines

Döpp, D., Hassan, A. A., Mourad, A.-F.-E., Nour El-Din, A. M., Angermund, K., Krüger, C., et al. (2003). New reaction of ethenetetracarbonitrile with N-arylisoindolines. Tetrahedron, 59(27), 5073-5081. doi:10.1016/S0040-4020(03)00735-X.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-000F-9865-0 Version Permalink: https://hdl.handle.net/21.11116/0000-0007-1593-B
Genre: Journal Article

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 Creators:
Döpp, Dietrich1, Author
Hassan, Alaa A.2, Author
Mourad, Aboul-Fetouh E.2, Author
Nour El-Din, Ahmed M.2, Author
Angermund, Klaus3, Author           
Krüger, Carl4, Author           
Lehmann, Christian W.5, Author           
Rust, Jörg5, Author           
Affiliations:
1Institut für Chemie, Universität Duisburg-Essen, D-47048 Duisburg, Germany, ou_persistent22              
2Department of Chemistry, Faculty of Science, El-Minia University, El-Minia, A.R. Egypt, ou_persistent22              
3Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              
4Service Department Krüger (XRAY), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445624              
5Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: cyano compounds; isoindoles; oxygenation; strained compounds
 Abstract: N-Arylisoindolines 1a–i react with ethenetetracarbonitrile 2 in aerated benzene by formation of [3-(2-aryl-3-dicyanomethylene-2,3-dihydro-1H-isoindol-1-ylidene)-2-aryl-2,3-dihydro-1H-isoindol-1-ylidene]propanedinitriles 8a–i (20–36%), N-aryl-3-dicyanomethylene-isoindol-2-ones 9a–i (15–21%) and N-arylphthalimides 10a–i (4–9%) as well as 1,1,2,2-tetracyanoethane 11 (35–55%). The structure of 8d has been unambiguously confirmed by a single crystal X-ray structure analysis. A rationale for the formation of products 8–11 is presented.

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Language(s): eng - English
 Dates: 2003-01-072003-05-022003-06-112003-06-30
 Publication Status: Issued
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/S0040-4020(03)00735-X
 Degree: -

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Title: Tetrahedron
  Other : Tetrahedron : the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry
Source Genre: Journal
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Publ. Info: Kidlington : Elsevier Science
Pages: - Volume / Issue: 59 (27) Sequence Number: - Start / End Page: 5073 - 5081 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/00404020