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ConjugatedSchiff bases. 15. substituent effect on the cycloaddition of heterocumulenes to some 1-oxa-4-azabutadienes

KonjugierteSchiff-Basen, 15. Mitt.: Substituenteneffekte bei der Cycloaddition einiger Heterocumulene mit 1-Oxa-4-azabutadienen

  • Organische Chemie Und Biochemie
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Abstract

The substituent effect on the cycloaddition of aryl isocyanates to some 1-oxa-4-azabutadienes has been investigated. It has been found that electron-withdrawing groups located in the aryl isocyanate ring distinctly increase the rate of the cycloaddition. The importance of isocyanate nitrogen unshared electrons has been considered. Rate constants and activation parameters have been discussed with respect to the mechanism.

Zusammenfassung

Der Substituenteneffekt bei der Cycloaddition von Arylisocyanaten an einige 1-Oxa-4-azabutadiene wurde untersucht. Es wurde festgestellt, daß e-anziehende Gruppen am Aryl-isocyanat-Ring deutlich die Geschwindigkeit der Cycloaddition erhöhen. Geschwindigkeitskonstanten und Aktivierungsparameter werden im Hinblick auf den Reaktionsmechanismus diskutiert.

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Author notes

  1. Janusz Moskal

    Present address: Department of Organic Chemistry, University of Groningen, 9747 AG, Groningen, The Netherlands

Authors and Affiliations

  1. Department of Organic Chemistry, University School of Kielce, PL-25020, Kielce, Poland

    Janusz Moskal & Alexandra Moskal

  2. Department of Organic Chemistry, Jagiellonian University, PL-30060, Krakow, Poland

    Piotr Milart

Authors
  1. Janusz Moskal
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  2. Alexandra Moskal
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  3. Piotr Milart
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Moskal, J., Moskal, A. & Milart, P. ConjugatedSchiff bases. 15. substituent effect on the cycloaddition of heterocumulenes to some 1-oxa-4-azabutadienes. Monatsh Chem 115, 187–195 (1984). https://doi.org/10.1007/BF00798409

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  • DOI: https://doi.org/10.1007/BF00798409

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