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Spezielle Reaktionen von α,β-ungesättigten Ketonen, 1. Mitt.: Über die Dimerisierung von 2-Benzyliden-1-indanon in Gegenwart starker Basen

Special reactions of α,β-unsaturated ketones, I. Dimerization of 2-benzylidene-1-indanone in the presence of strong bases

  • Organische Chemie Und Biochemie
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Abstract

Heating of 2-benzylidene-1-indanone (1) either in dimethylformamide in the presence of guanidine carbonate or inn-propanol in the presence of thiourea and sodium propylate yields a dimerP with the structure of 1,3-diphenyl-3a,8a-dihydrospiro{cyclopenta[a]indene-2,2′(1H,3′H)-indene}-1′,8(3H)-dione (7); this was deduced from the 400 MHz-1H- and 100MHz-13C-nmr-spectra and the corresponding two-dimensional HH- and CH-correlations. A possible mechanism for the formation of the spirocompound 7 is proposed; the stereo formula of the dimer7 K was established on the basis of a 400 MHz-HH-NOESY experiment.

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Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Universität Graz, A-8010, Graz, Österreich

    Winfried Wendelin & Karl Schermanz

  2. Institut für Organische Chemie und Biochemie, Universität Bonn, D-5300, Bonn, Bundesrepublik Deutschland

    Eberhard Breitmaier

Authors
  1. Winfried Wendelin
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  2. Karl Schermanz
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  3. Eberhard Breitmaier
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Wendelin, W., Schermanz, K. & Breitmaier, E. Spezielle Reaktionen von α,β-ungesättigten Ketonen, 1. Mitt.: Über die Dimerisierung von 2-Benzyliden-1-indanon in Gegenwart starker Basen. Monatsh Chem 119, 355–365 (1988). https://doi.org/10.1007/BF00810262

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  • DOI: https://doi.org/10.1007/BF00810262

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