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Zur Struktur der Produkte der Reaktion vonE/Z-1-Benzolsulfonyl-3-(1-pentenyl)-indol mit N-Phenylmaleinimid: Ein erster Beitrag zur Konfigurations- und Konformationsanalyse in der Vinylindol-Cycloadditionsreihe

Structure investigation of the products of the reaction ofE/Z-1-benzenesulfonyl-3-(1-pentenyl)-indole with N-phenylmaleimide: A first contribution to the analysis of configuration and conformation in the vinylindole cycloaddition series

  • Organische Chemie Und Biochemie
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Abstract

The products2,3 of the reaction ofE/Z-1-benzenesulfonyl-3-(1-pentenyl)-indole (1) and N-phenylmaleimide were analysed by1H-NMR spectroscopy. Exemplarily, the structure elucidation of theendo-cyclo-adduct2 b was achieved by using several NMR techniques (diff. NOE-, INDOR-measurements, decoupling experiments, spectra simulation). The1H-NMR-spectroscopically gained prediction of relative configuration and conformation of2 b was supported on X-ray analysis. The cyclohexene ring of the new cycloadducts adopts in the liquid phase and in the crystal a slightly twisted boat conformation.

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Authors and Affiliations

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

    Ludwig Pfeuffer, Ulf Pindur & Hans-Joachim Sattler

  2. Fachbereich Chemie, Philipps-Universität Marburg, D-3550, Marburg, Bundesrepublik Deutschland

    Werner Massa & Gerlinde Frenzen

Authors
  1. Ludwig Pfeuffer
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  2. Ulf Pindur
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  3. Hans-Joachim Sattler
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  4. Werner Massa
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  5. Gerlinde Frenzen
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Pfeuffer, L., Pindur, U., Sattler, HJ. et al. Zur Struktur der Produkte der Reaktion vonE/Z-1-Benzolsulfonyl-3-(1-pentenyl)-indol mit N-Phenylmaleinimid: Ein erster Beitrag zur Konfigurations- und Konformationsanalyse in der Vinylindol-Cycloadditionsreihe. Monatsh Chem 119, 1289–1297 (1988). https://doi.org/10.1007/BF00808309

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  • DOI: https://doi.org/10.1007/BF00808309

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