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New reaction of ethenetetracarbonitrile with N-arylisoindolines |
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| Authors: | Dietrich Dö pp,Alaa A HassanAboul-Fetouh E Mourad,Ahmed M Nour El-DinKlaus Angermund,Carl Krü gerChristian W Lehmann,Jö rg Rust |
| Affiliation: | a Institut für Chemie, Universität Duisburg-Essen, D-47048 Duisburg, Germany b Department of Chemistry, Faculty of Science, El-Minia University, El-Minia, A.R. Egypt c Max-Planck-Institut für Kohlenforschung, D-45466 Mülheim (Ruhr), Germany |
| 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. |
| Keywords: | cyano compounds isoindoles oxygenation strained compounds |
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