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Orthoamide und Iminiumsalze, C. Vinyloge Guanidiniumsalz-basierte ionische Flüssigkeiten sowie phenyloge Guanidiniumsalze und Orthoamide

  • Willi Kantlehner EMAIL logo , Heinz Malik and Ralf Kreß
Published/Copyright: July 27, 2020
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 75 Issue 6-7

Abstract

Cyclopropylacetylene and N,N,N′,N′,N′′,N′′-hexamethylguanidinium chloride (1a) react to give the orthoamide derivative 8c, in the presence of sodium hydride. 8c is transformed by elemental iodine to the vinylogous guanidinium salt 6f. Anion metathesis with the salts 5a, 5e, 6g delivers vinylogous guanidinium salts 5e–5i, 12a with counter ions derived from carbon acids (tricyanomethane, 1,1,3,3-tetracyano-propene). Phenylogous amidinium salts 15 guanidinium salts 19, 21 and the phenylogous orthoamide derivatives of formic acid 18 and carbonic acid 33 have been prepared.

Keywords: alkyne carbocylic acids; cleavage; orthoamides; phenylogous amidinium-salts; phenylogous guanidinium salts; phenylogous orthoamide derivatives; vinylogous guanidinium salts

Widmung: Herrn Professor Dr. Richard R. Schmidt zum 85. Geburtstag.

Corresponding author: Willi Kantlehner, Institut für Angewandte Forschung, Abteilung Technische Organische Synthesechemie und Katalyseforschung (TOSKA), Hochschule Aalen, Beethovenstr. 1, D-73430Aalen, Germany, and Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569Stuttgart, Germany, Fax: +49(7361) 5762250, E-mail:

Orthoamide und Iminiumsalze, IC see ref. [1]

Danksagung

Die vorliegende Arbeit wurde im Rahmen des Projekts „Produktentwicklung für Farbstoffsolarmodule“ der Landesstiftung Baden-Württemberg durchgeführt. Wir danken der BW-Stiftung für die finanzielle Unterstützung der Untersuchungen. Bei Herrn Prof. Dr. A. de Meijere, Göttingen, bedanken wir uns für die Überlassung von Cyclopropylacetylen.

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

  2. Research funding: State Foundation of Baden Württemberg.

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

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Received: 2019-12-18
Accepted: 2020-05-06
Published Online: 2020-07-27
Published in Print: 2020-08-27

© 2020 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research articles
  4. Derivatives of the triaminoguanidinium ion, 7: unsymmetrically substituted N,N',N''-triaminoguanidinium salts via a cyclopentanone spiroaminal intermediate
  5. Diethyl (iodoethynyl)phosphonate and (iodoethynyl)diphenylphosphane oxide: crystal structures and some cycloaddition reactions
  6. Synthesis, molecular structure and BSA-binding properties of a new binuclear Cd(II) complex based on 2-(1H-tetrazol-1-methyl)-1H-imidazole-4,5-dicarboxylic acid
  7. Microwave synthesis of a blue luminescent silver(I) coordination polymer with a rigid tris-triazole ligand
  8. Single-crystal structure determination of LaNi5–xInx and LaNi9–xIn2+x
  9. The reaction of imidazo[1,5-a]pyridines with ninhydrin revisited
  10. The syntheses, structures, and magnetic properties of two mononuclear manganese(II) complexes involving in situ hydrothermal decarboxylation
  11. A cobalt(II) coordination polymer constructed with the 2-carboxy-phenoxyacetate linker showing a corrugated layer structure: synthesis, structure analysis and magnetic properties
  12. Hexaniobate anions connected by [Ni(cyclam)]2+ complexes yield two interpenetrating three-dimensional networks
  13. High-pressure synthesis and crystal structure of the samarium meta-oxoborate γ-Sm(BO2)3
  14. High-pressure synthesis and characterization of the non-centrosymmetric scandium borate ScB6O9(OH)3
  15. Al5B12O25(OH) and Ga4InB12O25(OH) – two additional triel borates with the structure type M5B12O25(OH) (M = Ga, In)
  16. Al/N-based active Lewis pairs: isocyanate insertion products as efficient nucleophiles employed for the facile generation of highly functional molecules
  17. New compounds of the Li2MSn3S8 type
  18. Synthesis and magnetic properties of the extended RE4Pd9Al24 series (RE = Sc, Y, Ce–Nd, Sm, Gd–Lu)
  19. Solid solutions EuAu4Cd2−xMgx with a remarkably stable ferromagnetic ground state
  20. Mechanistic investigations on C–H activated dealkylating cyclo-amination reactions of substituted triazenes, formamidines and amidines
  21. Orthoamide und Iminiumsalze, IIC. Darstellung von N-(ω-Ammonioalkyl)-N,N′,N′,N″,N″-peralkylierten Guanidiniumsalzen und N-(ω-Aminoalkyl)-N′,N′,N″,N″-tetramethylguanidinen
  22. Orthoamide und Iminiumsalze, IC. Synthese und Reaktionen von N,N,N′,N′,N′′-Pentaalkyl-N′′-[2-(N,N,N′,N′,N′′-pentaalkylguanidinio)ethyl]-guanidiniumsalzen
  23. Orthoamide und Iminiumsalze, C. Vinyloge Guanidiniumsalz-basierte ionische Flüssigkeiten sowie phenyloge Guanidiniumsalze und Orthoamide
  24. Notes
  25. La5Ir1.73In4.27 with Lu5Ni2In4-type structure
  26. The scandium-rich indide Sc50Pt13.47In2.53
https://doi.org/10.1515/znb-2019-0231
Keywords for this article
alkyne carbocylic acids; cleavage; orthoamides; phenylogous amidinium-salts; phenylogous guanidinium salts; phenylogous orthoamide derivatives; vinylogous guanidinium salts

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research articles
  4. Derivatives of the triaminoguanidinium ion, 7: unsymmetrically substituted N,N',N''-triaminoguanidinium salts via a cyclopentanone spiroaminal intermediate
  5. Diethyl (iodoethynyl)phosphonate and (iodoethynyl)diphenylphosphane oxide: crystal structures and some cycloaddition reactions
  6. Synthesis, molecular structure and BSA-binding properties of a new binuclear Cd(II) complex based on 2-(1H-tetrazol-1-methyl)-1H-imidazole-4,5-dicarboxylic acid
  7. Microwave synthesis of a blue luminescent silver(I) coordination polymer with a rigid tris-triazole ligand
  8. Single-crystal structure determination of LaNi5–xInx and LaNi9–xIn2+x
  9. The reaction of imidazo[1,5-a]pyridines with ninhydrin revisited
  10. The syntheses, structures, and magnetic properties of two mononuclear manganese(II) complexes involving in situ hydrothermal decarboxylation
  11. A cobalt(II) coordination polymer constructed with the 2-carboxy-phenoxyacetate linker showing a corrugated layer structure: synthesis, structure analysis and magnetic properties
  12. Hexaniobate anions connected by [Ni(cyclam)]2+ complexes yield two interpenetrating three-dimensional networks
  13. High-pressure synthesis and crystal structure of the samarium meta-oxoborate γ-Sm(BO2)3
  14. High-pressure synthesis and characterization of the non-centrosymmetric scandium borate ScB6O9(OH)3
  15. Al5B12O25(OH) and Ga4InB12O25(OH) – two additional triel borates with the structure type M5B12O25(OH) (M = Ga, In)
  16. Al/N-based active Lewis pairs: isocyanate insertion products as efficient nucleophiles employed for the facile generation of highly functional molecules
  17. New compounds of the Li2MSn3S8 type
  18. Synthesis and magnetic properties of the extended RE4Pd9Al24 series (RE = Sc, Y, Ce–Nd, Sm, Gd–Lu)
  19. Solid solutions EuAu4Cd2−xMgx with a remarkably stable ferromagnetic ground state
  20. Mechanistic investigations on C–H activated dealkylating cyclo-amination reactions of substituted triazenes, formamidines and amidines
  21. Orthoamide und Iminiumsalze, IIC. Darstellung von N-(ω-Ammonioalkyl)-N,N′,N′,N″,N″-peralkylierten Guanidiniumsalzen und N-(ω-Aminoalkyl)-N′,N′,N″,N″-tetramethylguanidinen
  22. Orthoamide und Iminiumsalze, IC. Synthese und Reaktionen von N,N,N′,N′,N′′-Pentaalkyl-N′′-[2-(N,N,N′,N′,N′′-pentaalkylguanidinio)ethyl]-guanidiniumsalzen
  23. Orthoamide und Iminiumsalze, C. Vinyloge Guanidiniumsalz-basierte ionische Flüssigkeiten sowie phenyloge Guanidiniumsalze und Orthoamide
  24. Notes
  25. La5Ir1.73In4.27 with Lu5Ni2In4-type structure
  26. The scandium-rich indide Sc50Pt13.47In2.53
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