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Diels-Alder reaction of fulvenes with N-(3,5-dichlorophenyl)-maleimide

Diels-Alder — Reaktion von Fulvenen mit N-(3,5-Dichlorphenyl)-maleinsäureimid

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

N-(3,5-Dichlorophenyl)-maleimide reacts smoothly with a variety of substituted fulvenes (1) to give onlyendo adducts (3) independent of the nature of fulvene substituent,Lewis acid catalyst, and reaction solvent and temperature. The structure of theDiels-Alder adduct3f was determined by X-ray crystallography. Semi-empirical quantum methods (AM1) were used to rationalize theendo stereoselectivity.

Zusammenfassung

N-(3,5-Dichlorphenyl)-maleinsäureimid reagiert glatt mit einer Anzahl substituierter Fulvene (1) zu ausschließlichendo-konfigurierten Addukten (3), unabhängig von der Natur des Substituenten am Fulven, vomLewis-Katalysator und von Lösungsmittel und Reaktionstemperatur. Die Struktur desDiels-Alder — Addukts3f wurde durch Röntgenstrukturanalyse bestimmt. Dieendo-Stereoselektivität wird mittels semiempirischer quantenmechanischer Methoden (AM1) verständlich gemacht.

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Authors and Affiliations

  1. Department of Organic Chemistry, Slovak Technical University, SK-81237, Batislava, Slovak Republic

    V. Ondrus & L' Fisera

  2. Department of Organic Chemistry, University of Munich, D-80333, Munich, Germany

    K. Polborn

  3. Institute of Chemistry, Comenius University, SK-84215, Bratislava, Slovak Republic

    P. Ertl

  4. Central Laboratory of Chemical Techniques, Slovak Technical University, SK-81237, Bratislava, Slovak Republic

    N. Prónayová

Authors
  1. V. Ondrus
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  2. L' Fisera
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  3. K. Polborn
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  4. P. Ertl
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  5. N. Prónayová
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Dedicated to Professor Fritz Sauter on the occasion of his 65th birthday

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Ondrus, V., Fisera, L., Polborn, K. et al. Diels-Alder reaction of fulvenes with N-(3,5-dichlorophenyl)-maleimide. Monatsh Chem 126, 961–969 (1995). https://doi.org/10.1007/BF00811016

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  • DOI: https://doi.org/10.1007/BF00811016

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