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Journal Article

New reaction of ethenetetracarbonitrile with N-arylisoindolines

MPS-Authors
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Angermund,  Klaus
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Krüger,  Carl
Service Department Krüger (XRAY), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lehmann,  Christian W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Rust,  Jörg
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

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.


Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-9865-0
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.