Home Zur Reaktion von 2,4-Dioxo-4-ferrocenyl-butansäureethylester mit primären aromatischen Aminen / On the Reaction of Ethyl 2,4-Dioxo-4-ferrocenyl-butanoate with Primary Aromatic Amines
Article
Licensed
Unlicensed Requires Authentication

Zur Reaktion von 2,4-Dioxo-4-ferrocenyl-butansäureethylester mit primären aromatischen Aminen / On the Reaction of Ethyl 2,4-Dioxo-4-ferrocenyl-butanoate with Primary Aromatic Amines

  • Petra Prokop , Rainer Richter and Lothar Beyer
Published/Copyright: June 2, 2014
Become an author with De Gruyter Brill
Author Information Explore this Subject
Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 54 Issue 7

Starting from ethyl 2,4-dioxo-4-ferrocenyl-butanoate (1) a series of new ferrocene derivatives has been prepared. While the reaction with o-phenylene diamine leads to two ferrocene-containing heterocyclic compounds, 4-ferrocenyl-3H-1,5-benzodiazepine-2-carbonic acid ethyl ester (3) and 3-(2-ferrocenyl-2-oxo-ethylidene)-3,4-dihydro-1H-quinoxalin-2-one · H20 (4), reactions with m- and p-phenylene diamine give both the mono- and disubstituted products 5 - 8, respectively. The conversion of 4 by Lawesson’s reagent results in 2-ferrocenvl-thieno[2,3- b]quinoxaline (9). The new compounds have been characterized by their 1H, 13C NMR, and mass spectra. The molecular structures of 4-ferrocenyl-4-oxo-2-phenylamino-but-2-enoic acid ethyl ester 2, and of 4 and 9 have been determined by X-ray crystal structure analysis.

Keywords: Ferrocene; β-Diketones; Enaminoketones; NMR Data; Crystal Structure
Received: 1999-3-12
Published Online: 2014-6-2
Published in Print: 1999-7-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Titelei
  2. The Structural Chemistry of GoId(I) Quinoline-2-thiolate and Iodide Complexes of Polytertiary Phosphines
  3. EPR-Einkristall-Untersuchungen an (n-Bu4N)2[Cu(dmit)2] im antiferromagnetisch gekoppelten Wirtsgitter (n-Bu4N)2[(dmit)Cu(tto)Cu(dmit)]: Ein Beitrag zur Aufklärung der sogenannten „paramagnetischen Verunreinigung“ im Wirtsgitter / A Single Crystal EPR Investigation on (n-Bu4N)2[Cu(dmit)2] in the Antiferromagnetically Coupled Host Lattice (n-Bu4N)2[(dmit)Cu(tto)Cu(dmit)]: A Contribution to the Nature of the So-called “Paramagnetic Impurities”
  4. Reaktionen von [(η5-C5R5)2WH2] mit Boranen / Reactions of [(η5-C5R5)2WH2] with Boranes
  5. [Ni(NH3 )6]S04 : Kristallstruktur und Infrarotspektren / [Ni(NH3)6]SO4: Crystal Structure and Infrared Spectra
  6. Zur Reaktion von 2,4-Dioxo-4-ferrocenyl-butansäureethylester mit primären aromatischen Aminen / On the Reaction of Ethyl 2,4-Dioxo-4-ferrocenyl-butanoate with Primary Aromatic Amines
  7. Complexes of N-Aryltriphenylphosphinimines with Mercury(II) Halides
  8. Condensed [Ru4Sn6] Units in the Stannides LnRu4Sn6 (Ln = La, Pr, Nd, Sm, Gd) - Synthesis, Structure, and Chemical Bonding
  9. Neutronen- und Röntgenbeugungsuntersuchungen an Pulvern und Einkristallen von Strukturverwandten des Berliner Blaus: CsMnIICrIII(CN)6 · D2O , NMe4MnII(Cr0,06,Mn0,94)III(CN)6 · 8 H2O , NMe4MnIICoIII(CN)6 · 8 H20 , Mn3II[MnIII(CN)6]2 · 15 H2O und Cd3[FeIII(CN)6]2 · 15 H2O / Neutron and X-Ray Diffraction Studies on Powders and Single Crystals of Compounds Structurally Related to Prussian Blue: CsMnIICrIII(CN)6 · D2O, NMe4MnII(Cr0,06Mn0,94)III(CN)6 · 8 H2O, NMe4MnIICoIII(CN)6 · 8 H2O, Mn3II[MnIII(CN)6]2 · 15 H2O and Cd3[FeIII(CN)6]2 · 15 H2O
  10. Über das Octastannandiid R*6Sn8[Na(THF)2 ]2 und zur möglichen Existenz des Octastannans R*6Sn8 [1] / On an Octastannanediide R*6Sn8[Na(THF)2]2 and the Possible Existence of an Octastannane R*6Sn8 [1]
  11. Ligandenaustauschreaktionen von NiCl2 (PPh3)2 mit O(S)⌒N⌒S-Liganden / Ligand Exchange Reactions of NiCl2(PPh3)2 with O(S )⌒ N ⌒ S Ligands
  12. Bis(n-pentanethiolato)mercury(II), Hg(SC5H11)2 - Preparation, Characterization, Crystal and Molecular Structure; Reactivity towards Organic Thiols
  13. K[B6PO10(OH)4]: Ein Borophosphat mit gestreckten Bändern aus Tetraeder-Vierer-Ringen und offen-zyklischen Verzweigungen über planare B2O3(OH)2-Gruppen / K[B6PO10(OH)4]: A Borophosphate Containing Rods of Tetrahedral Vierer-Rings with Additional Open-Loop Branchings via Planar B2O3(OH)2 Groups
  14. Mixed-Sandwich η5/η7 Vanadium Complexes. The Molecular Structure of (η5-2-Methyl-indenyl)-(η7-cycloheptatrienyl)-vanadium
  15. Antimony as a Donor Atom in Silver Coordination Chemistry: Synthesis, IR Spectra and Structure of the Silver(I) Cyanoximate Complexes with Triphenylstibine and Triphenylphosphine Model Compounds
  16. Reaktionen von Isochinolinium-Salzen mit Hydroxylamin-Derivaten, 3. Mitteilung. Mechanismus der Aminoxid-Bildung / Reactions of Isoquinolinium Salts with Hydroxylamine Derivatives, 3rd Communication. Mechanism of Amine Oxide Generation
  17. Alkyl Heteroaromatics as Building Blocks in Organic Synthesis: The Reactivity of Alkyl Azoles toward Electrophilic Reagents
  18. Electronic Structure of 2,6-Bis{.N-(2-hydroxyphenyl)immoinethyl}-4-methylphenol
  19. Two New Aromatic Constituents from Stocksia brahuica
  20. Structure and Conformation of Tetra-meso-, Octa-β-, and Dodecasubstituted 22,24-Dihydroporphyrins (Porphyrin Dications)
  21. Organoactinide Chemistry: Polysilylated Actinidocenes of Thorium, Uranium, and Neptunium
https://doi.org/10.1515/znb-1999-0705
Keywords for this article
Ferrocene; β-Diketones; Enaminoketones; NMR Data; Crystal Structure

Articles in the same Issue

  1. Titelei
  2. The Structural Chemistry of GoId(I) Quinoline-2-thiolate and Iodide Complexes of Polytertiary Phosphines
  3. EPR-Einkristall-Untersuchungen an (n-Bu4N)2[Cu(dmit)2] im antiferromagnetisch gekoppelten Wirtsgitter (n-Bu4N)2[(dmit)Cu(tto)Cu(dmit)]: Ein Beitrag zur Aufklärung der sogenannten „paramagnetischen Verunreinigung“ im Wirtsgitter / A Single Crystal EPR Investigation on (n-Bu4N)2[Cu(dmit)2] in the Antiferromagnetically Coupled Host Lattice (n-Bu4N)2[(dmit)Cu(tto)Cu(dmit)]: A Contribution to the Nature of the So-called “Paramagnetic Impurities”
  4. Reaktionen von [(η5-C5R5)2WH2] mit Boranen / Reactions of [(η5-C5R5)2WH2] with Boranes
  5. [Ni(NH3 )6]S04 : Kristallstruktur und Infrarotspektren / [Ni(NH3)6]SO4: Crystal Structure and Infrared Spectra
  6. Zur Reaktion von 2,4-Dioxo-4-ferrocenyl-butansäureethylester mit primären aromatischen Aminen / On the Reaction of Ethyl 2,4-Dioxo-4-ferrocenyl-butanoate with Primary Aromatic Amines
  7. Complexes of N-Aryltriphenylphosphinimines with Mercury(II) Halides
  8. Condensed [Ru4Sn6] Units in the Stannides LnRu4Sn6 (Ln = La, Pr, Nd, Sm, Gd) - Synthesis, Structure, and Chemical Bonding
  9. Neutronen- und Röntgenbeugungsuntersuchungen an Pulvern und Einkristallen von Strukturverwandten des Berliner Blaus: CsMnIICrIII(CN)6 · D2O , NMe4MnII(Cr0,06,Mn0,94)III(CN)6 · 8 H2O , NMe4MnIICoIII(CN)6 · 8 H20 , Mn3II[MnIII(CN)6]2 · 15 H2O und Cd3[FeIII(CN)6]2 · 15 H2O / Neutron and X-Ray Diffraction Studies on Powders and Single Crystals of Compounds Structurally Related to Prussian Blue: CsMnIICrIII(CN)6 · D2O, NMe4MnII(Cr0,06Mn0,94)III(CN)6 · 8 H2O, NMe4MnIICoIII(CN)6 · 8 H2O, Mn3II[MnIII(CN)6]2 · 15 H2O and Cd3[FeIII(CN)6]2 · 15 H2O
  10. Über das Octastannandiid R*6Sn8[Na(THF)2 ]2 und zur möglichen Existenz des Octastannans R*6Sn8 [1] / On an Octastannanediide R*6Sn8[Na(THF)2]2 and the Possible Existence of an Octastannane R*6Sn8 [1]
  11. Ligandenaustauschreaktionen von NiCl2 (PPh3)2 mit O(S)⌒N⌒S-Liganden / Ligand Exchange Reactions of NiCl2(PPh3)2 with O(S )⌒ N ⌒ S Ligands
  12. Bis(n-pentanethiolato)mercury(II), Hg(SC5H11)2 - Preparation, Characterization, Crystal and Molecular Structure; Reactivity towards Organic Thiols
  13. K[B6PO10(OH)4]: Ein Borophosphat mit gestreckten Bändern aus Tetraeder-Vierer-Ringen und offen-zyklischen Verzweigungen über planare B2O3(OH)2-Gruppen / K[B6PO10(OH)4]: A Borophosphate Containing Rods of Tetrahedral Vierer-Rings with Additional Open-Loop Branchings via Planar B2O3(OH)2 Groups
  14. Mixed-Sandwich η5/η7 Vanadium Complexes. The Molecular Structure of (η5-2-Methyl-indenyl)-(η7-cycloheptatrienyl)-vanadium
  15. Antimony as a Donor Atom in Silver Coordination Chemistry: Synthesis, IR Spectra and Structure of the Silver(I) Cyanoximate Complexes with Triphenylstibine and Triphenylphosphine Model Compounds
  16. Reaktionen von Isochinolinium-Salzen mit Hydroxylamin-Derivaten, 3. Mitteilung. Mechanismus der Aminoxid-Bildung / Reactions of Isoquinolinium Salts with Hydroxylamine Derivatives, 3rd Communication. Mechanism of Amine Oxide Generation
  17. Alkyl Heteroaromatics as Building Blocks in Organic Synthesis: The Reactivity of Alkyl Azoles toward Electrophilic Reagents
  18. Electronic Structure of 2,6-Bis{.N-(2-hydroxyphenyl)immoinethyl}-4-methylphenol
  19. Two New Aromatic Constituents from Stocksia brahuica
  20. Structure and Conformation of Tetra-meso-, Octa-β-, and Dodecasubstituted 22,24-Dihydroporphyrins (Porphyrin Dications)
  21. Organoactinide Chemistry: Polysilylated Actinidocenes of Thorium, Uranium, and Neptunium
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 8.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/znb-1999-0705/html
Scroll to top button