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Synthesis and properties of unique mesoionic 1,3-thiazolium-4-olates

Synthese und Eigenschaften einzigartiger Mesoionischer 1,3-Thiazolium-4-olate

  • Organische Chemie Und Biochemie
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Summary

N-bridged 1,3-thiazolium-4-olates were synthesized by reaction of 3-substituted 3-aminothioacrylanilides with bromoacetic acid ethyl ester in refluxing xylene. Their structural aspects were investigated by means of mass, NMR, and absorption spectroscopy. They display an unusual ring-chain tautomeric equilibrium, which is governed by the nature of the solvents and thepH value.

Zusammenfassung

N-verbrückte 1,3-Thiazolium-4-olate wurden durch Reaktion von 3-substitutierten 3-Aminothioacrylaniliden mit Bromessigsäureethylester in siedendem Xylol synthetisiert. Ihre strukturellen Aspekte wurden mit Hilfe von Massen-, NMR- und Absorptionsspektroskopie untersucht. Sie zeigen ein ungewöhnliches Ring-Ketten-Tautomeriegleichgewicht, das durch die Natur des Lösungsmittels und denpH-Wert gesteuert wird.

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Authors and Affiliations

  1. Department of Organic Chemistry, Jagiellonian University, PL-30060, Kraków, Poland

    B. Zaleska & D. Ciez

  2. Institute of Chemistry, Johannes Kepler University, A-4040, Linz, Austria

    H. Falk

Authors
  1. B. Zaleska
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  2. D. Ciez
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  3. H. Falk
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Zaleska, B., Ciez, D. & Falk, H. Synthesis and properties of unique mesoionic 1,3-thiazolium-4-olates. Monatsh Chem 127, 1251–1257 (1996). https://doi.org/10.1007/BF00807792

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  • DOI: https://doi.org/10.1007/BF00807792

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