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 |
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| Authors: | Ludwig Pfeuffer Ulf Pindur Hans-Joachim Sattler Werner Massa Gerlinde Frenzen |
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| Affiliation: | (1) Institut für Pharmazie, Fachbereich Chemie und Pharmazie, Universität Mainz, D-6500 Mainz 1, Bundesrepublik Deutschland;(2) Fachbereich Chemie, Philipps-Universität Marburg, D-3550 Marburg, Bundesrepublik Deutschland |
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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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| Keywords: | 3-Vinylindoles Cycloadducts 1H-NMR X-Ray analysis |
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