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New structural aspects of 3-vinyl-1H-indoles for predicting the outcome of Diels-Alder reactions

Neue strukturelle Aspekte von 3-Vinylindolen zur Vorhersage der Reaktionsergebnisse bei Diels-Alder-Reaktionen

  • Organische Chemie Und Biochemie
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Summary

Some selected 3-vinyl-1H-indoles have been synthesised and the first13C-NMR studies performed; in addition He(Iα) photoelectron spectra and the results of perturbation MO calculations of some examples of this class of compounds are presented. The molecular characteristics obtained thereby can be used to predict the results of [π4s+π2s]-cycloaddition reactions with 3-vinylindoles.

Zusammenfassung

An selektiv synthetisierten 3-Vinyl-1H-indolen werden erstmals13C-NMR-spektroskopische Studien durchgeführt und exemplarisch an einigen Vertretern dieser Strukturklasse He(Iα)-Photoelektronenspektren sowie Ergebnisse von Störungs-MO-Rechnungen vorgestellt. Die daraus gewonnenen Moleküleigenschaften können zur Vorhersage des Reaktionsausganges von [π4s+π2s]-Cycloadditionen mit 3-Vinylindolen verwendent werden.

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Authors and Affiliations

  1. Institut für Pharmazie, Fachbereich Chemie und Pharmazie, Universität Mainz, D-6500, Mainz 1, Germany

    Ulf Pindur & Ludwig Pfeuffer

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  1. Ulf Pindur
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  2. Ludwig Pfeuffer
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Pindur, U., Pfeuffer, L. New structural aspects of 3-vinyl-1H-indoles for predicting the outcome of Diels-Alder reactions. Monatsh Chem 120, 27–34 (1989). https://doi.org/10.1007/BF00809646

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  • DOI: https://doi.org/10.1007/BF00809646

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