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1-Trifluoromethyl-prop-2-yne 1-iminium salts and 1-imines: reactions with the mesoionic „Nitron“

  • Gerhard Maas ORCID logo EMAIL logo and Raphael Koch
Published/Copyright: November 23, 2020
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 75 Issue 12

Abstract

The heterocyclic mesoionic compound (1,4-diphenyl-1H-1,2,4-triazol-4-ium-3-yl)(phenyl)amide („Nitron“) has recently been found to exist in a prototropic equilibrium with minor amounts of a nucleophilic heterocyclic carbene of the 1,2,4-triazolyl-5-ylidene type. Here we report that Nitron reacts with 1-trifluoromethyl-substituted prop-2-yne iminium salts by conjugate nucleophilic addition of the anionic PhN‒ substituent in the mesoionic tautomer, whereas the nucleophilic triazolylidene form is involved in the reaction with 1-CF3-prop-2-yne imines. 3-(2,3-Dihydro-1H-benzo[c]azepin-5-yl)-1H-1,2,4-triazol-4-ium triflate salts were obtained in the former case and (Z)-9-arylidene-1,2,4,7-tetraazaspiro[4.4]nona-2,7-dienes in the latter.

Keywords: acetylenic imines; acetylenic iminium salts; mesoionic betaine; N-heterocyclic carbene; 1,2,4-triazol-5-ylidene
Corresponding author: Gerhard Maas, Institute of Organic Chemistry I, Ulm University, Albert-Einstein-Allee 11, D-89081Ulm, Germany, E-mail:

Acknowledgments

We thank B. Müller (Institute of Inorganic Chemistry II) for the collection of the X-ray diffraction data and Dr. M. Wunderlin for obtaining the mass spectra.

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Ulm University.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2020-0178).

Received: 2020-11-02
Accepted: 2020-11-11
Published Online: 2020-11-23
Published in Print: 2020-12-16

© 2020 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research Articles
  4. A zinc(II) coordination polymer based on a flexible bis(benzimidazole) ligand: synthesis, crystal structure and fluorescence study
  5. A study of antituberculosis activities and crystal structures of (E)-2-[2-(arylidene)hydrazinyl]pyrimidine and (E)-N1-(arylidene)pyrimidine-2-carbohydrazide derivatives
  6. Pt3Ni/C and Pt3Co/C cathodes as electrocatalysts for use in oxygen sensors and proton exchange membrane fuel cells
  7. Selective cyclization modes of methyl 3′-heteroarylamino-2′-(2,5-dichlorothiophene-3-carbonyl)acrylates. Synthesis of model (thienyl)pyrazolo- and triazolo[1,5-α]pyrimidines
  8. Synthesis and crystal structures of two new lead(II) complexes with the pincer-type ligand 4′-(4-chlorophenyl)-2,2′:6′,2″-terpyridine (Cl-Ph-tpy): subtle interplay of weak intermolecular interactions
  9. Die unerwartete Kristallstruktur des Cäsium-Dodekahydro-Monocarba-closo-Dodekaborats Cs[CB11H12]
  10. Synthesis, crystal structure and photoluminescence of a binuclear rhenium(I) carbonyl complex incorporated in a framework of a distorted salophen ligand
  11. 1-Trifluoromethyl-prop-2-yne 1-iminium salts and 1-imines: reactions with the mesoionic „Nitron“
  12. Note
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https://doi.org/10.1515/znb-2020-0178
Keywords for this article
acetylenic imines; acetylenic iminium salts; mesoionic betaine; N-heterocyclic carbene; 1,2,4-triazol-5-ylidene

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research Articles
  4. A zinc(II) coordination polymer based on a flexible bis(benzimidazole) ligand: synthesis, crystal structure and fluorescence study
  5. A study of antituberculosis activities and crystal structures of (E)-2-[2-(arylidene)hydrazinyl]pyrimidine and (E)-N1-(arylidene)pyrimidine-2-carbohydrazide derivatives
  6. Pt3Ni/C and Pt3Co/C cathodes as electrocatalysts for use in oxygen sensors and proton exchange membrane fuel cells
  7. Selective cyclization modes of methyl 3′-heteroarylamino-2′-(2,5-dichlorothiophene-3-carbonyl)acrylates. Synthesis of model (thienyl)pyrazolo- and triazolo[1,5-α]pyrimidines
  8. Synthesis and crystal structures of two new lead(II) complexes with the pincer-type ligand 4′-(4-chlorophenyl)-2,2′:6′,2″-terpyridine (Cl-Ph-tpy): subtle interplay of weak intermolecular interactions
  9. Die unerwartete Kristallstruktur des Cäsium-Dodekahydro-Monocarba-closo-Dodekaborats Cs[CB11H12]
  10. Synthesis, crystal structure and photoluminescence of a binuclear rhenium(I) carbonyl complex incorporated in a framework of a distorted salophen ligand
  11. 1-Trifluoromethyl-prop-2-yne 1-iminium salts and 1-imines: reactions with the mesoionic „Nitron“
  12. Note
  13. YIrIn with ZrNiAl-type structure
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