Synthesis of a Phenylazo-derivative of a 1,2,3-thiadiazolium Methylide - C-13/n-15 Nmr Characterization and Crystal-structure Analysis

Labbe, Gérard;Frederix, A.;Toppet, S.;Declercq, Jean-Paul
(1991) Journal of Heterocyclic Chemistry : international journal — Vol. 28, n° 2, p. 477-480 (1991)

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  • Labbe, GérardUCLouvain
    Author
  • Frederix, A.
    Author
  • Toppet, S.
    Author
  • Declercq, Jean-PaulUCLouvain
    Author
Abstract
The N-phenylhydrazone derived from 4-methoxycarbonyl-1,2,3-thiadiazole-5-carbaldehyde 6 is methylated at the N-3 position, yielding the mesoionic compound 8. The C-13 and N-15 nmr data, as well as the results from a crystal structure analysis, indicate that the molecule is best represented by the resonance forms 8A and 8B. Comparison is made with the previously synthesized thiadiazole derivative 2 which possesses thiapentalene characteristics.
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Labbe, G., Frederix, A., Toppet, S., & Declercq, J.-P. (1991). Synthesis of a Phenylazo-derivative of a 1,2,3-thiadiazolium Methylide - C-13/n-15 Nmr Characterization and Crystal-structure Analysis. Journal of Heterocyclic Chemistry : international journal, 28(2), 477-480. https://doi.org/10.1002/jhet.5570280252 (Original work published 1991)