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New Indigoid Compounds by Reduction of Bis-Imidoylchlorides of Oxalic Acid – A Further Evidence for Dimeric Isocyanides?

Neue indigoide Verbindungen durch Reduktion von Bis-imidoylchloriden der Oxalsäure – ein weiterer Beweis für dimere Isocyanide?

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Summary.

 Bis-imidoylchlorides of oxalic acid react rapidly with magnesium shreds in dry THF under ultrasonic conditions to give 1,5-naphthyridine derivatives and the isomeric indigodianiles. Using a cross-over experiment the existence of key intermediates corresponding to dimeric isocyanides could be verified.

Zusammenfassung.

 Bis-imidoylchloride der Oxalsäure reagieren mit Magnesiumspänen in trockenem THF und unter Ultraschallbedingungen zu den 1,5-Naphthyridinderivaten und den isomeren Indigodianilen. Durch Untersuchungen des Reaktionsmechanismus konnten Hinweise auf radikalische C2-Schlüsselintermediate vom Typ dimerer Isocyanide erbracht werden.

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Authors and Affiliations

  1.  Institut für Organische und Makromolekulare Chemie, Friedrich-Schiller-Universität, D-07743 Jena, Germany, DE

    Matthias Wenzel, Rainer Beckert & Wolfgang Günther

  2.  Institut für Anorganische und Analytische Chemie, Friedrich-Schiller-Universität, D-07743 Jena, Germany, DE

    Helmar Görls

  3.  Institut für Analytische Chemie, Chemo- und Biosensorik, Universität Regensburg, D-93053 Regensburg, Germany, DE

    Frank Lehmann

Authors
  1. Matthias Wenzel
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  2. Frank Lehmann
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  3. Rainer Beckert
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  4. Wolfgang Günther
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  5. Helmar Görls
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Additional information

Received April 26, 1999. Accepted May 25, 1999

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Wenzel, M., Lehmann, F., Beckert, R. et al. New Indigoid Compounds by Reduction of Bis-Imidoylchlorides of Oxalic Acid – A Further Evidence for Dimeric Isocyanides?. Monatshefte fuer Chemie 130, 1373–1382 (1999). https://doi.org/10.1007/PL00010197

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  • DOI: https://doi.org/10.1007/PL00010197

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