Diels-Alder reaction of fulvenes with N-(3,5-dichlorophenyl)-maleimide |
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| Authors: | V. Ondrus L' Fisera K. Polborn P. Ertl N. Prónayová |
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| Affiliation: | (1) Department of Organic Chemistry, Slovak Technical University, SK-81237 Batislava, Slovak Republic;(2) Department of Organic Chemistry, University of Munich, D-80333 Munich, Germany;(3) Institute of Chemistry, Comenius University, SK-84215 Bratislava, Slovak Republic;(4) Central Laboratory of Chemical Techniques, Slovak Technical University, SK-81237 Bratislava, Slovak Republic |
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| Abstract: | 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.Dedicated to Professor Fritz Sauter on the occasion of his 65th birthday |
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| Keywords: | Fulvene derivatives Stereoselectivity ofDiels-Alder cycloadditions AM1 calculations |
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