An efficient iminophosphorane-mediated synthesis, NMR-IR spectroscopic and X-ray study of novel ferrocenylimidazole derivatives: Part 10. Study on ferrocenes

György Túrós, A. Csámpai, M. Czugler, Heinrich Wamhoff, P. Sohár

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19 Citations (Scopus)

Abstract

Starting from ethyl β-ferrocenyl-α-azidoacrylate (2), a series of novel 4-ferrocenylidene-1-aminoimidazolones (6a-j) was prepared in a pathway involving an aza-Wittig reaction followed by condensation of the resulting carbodiimidoester with hydrazines. Formation of [1,2,4]triazines of type 7 was not observed. Simultaneously with the formation of 2, an interesting transformation was also observed to afford a novel imidazolone derivative (3) containing two ferrocenyl groups. The structures of the products were determined by IR, 1H- and 13C-NMR spectroscopy (including 2D-COSY, DEPT, 2D-HMQC, and 2D-HMBC measurements), and in the case of compound 3 also by single-crystal X-ray analysis.

Original languageEnglish
Pages (from-to)122-130
Number of pages9
JournalJournal of Organometallic Chemistry
Volume634
Issue number2
DOIs
Publication statusPublished - Sep 21 2001

Fingerprint

Hydrazines
ferrocenes
Hydrazine
X ray analysis
Nuclear magnetic resonance spectroscopy
Condensation
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
X-Rays
Single crystals
Derivatives
X rays
nuclear magnetic resonance
hydrazines
synthesis
x rays
condensation
single crystals
products
spectroscopy

Keywords

  • Ferrocenes
  • Ferrocenylimidazole derivatives
  • Iminophosphorane
  • NMR
  • Structure elucidation by IR
  • X-ray

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

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title = "An efficient iminophosphorane-mediated synthesis, NMR-IR spectroscopic and X-ray study of novel ferrocenylimidazole derivatives: Part 10. Study on ferrocenes",
abstract = "Starting from ethyl β-ferrocenyl-α-azidoacrylate (2), a series of novel 4-ferrocenylidene-1-aminoimidazolones (6a-j) was prepared in a pathway involving an aza-Wittig reaction followed by condensation of the resulting carbodiimidoester with hydrazines. Formation of [1,2,4]triazines of type 7 was not observed. Simultaneously with the formation of 2, an interesting transformation was also observed to afford a novel imidazolone derivative (3) containing two ferrocenyl groups. The structures of the products were determined by IR, 1H- and 13C-NMR spectroscopy (including 2D-COSY, DEPT, 2D-HMQC, and 2D-HMBC measurements), and in the case of compound 3 also by single-crystal X-ray analysis.",
keywords = "Ferrocenes, Ferrocenylimidazole derivatives, Iminophosphorane, NMR, Structure elucidation by IR, X-ray",
author = "Gy{\"o}rgy T{\'u}r{\'o}s and A. Cs{\'a}mpai and M. Czugler and Heinrich Wamhoff and P. Soh{\'a}r",
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T1 - An efficient iminophosphorane-mediated synthesis, NMR-IR spectroscopic and X-ray study of novel ferrocenylimidazole derivatives

T2 - Part 10. Study on ferrocenes

AU - Túrós, György

AU - Csámpai, A.

AU - Czugler, M.

AU - Wamhoff, Heinrich

AU - Sohár, P.

PY - 2001/9/21

Y1 - 2001/9/21

N2 - Starting from ethyl β-ferrocenyl-α-azidoacrylate (2), a series of novel 4-ferrocenylidene-1-aminoimidazolones (6a-j) was prepared in a pathway involving an aza-Wittig reaction followed by condensation of the resulting carbodiimidoester with hydrazines. Formation of [1,2,4]triazines of type 7 was not observed. Simultaneously with the formation of 2, an interesting transformation was also observed to afford a novel imidazolone derivative (3) containing two ferrocenyl groups. The structures of the products were determined by IR, 1H- and 13C-NMR spectroscopy (including 2D-COSY, DEPT, 2D-HMQC, and 2D-HMBC measurements), and in the case of compound 3 also by single-crystal X-ray analysis.

AB - Starting from ethyl β-ferrocenyl-α-azidoacrylate (2), a series of novel 4-ferrocenylidene-1-aminoimidazolones (6a-j) was prepared in a pathway involving an aza-Wittig reaction followed by condensation of the resulting carbodiimidoester with hydrazines. Formation of [1,2,4]triazines of type 7 was not observed. Simultaneously with the formation of 2, an interesting transformation was also observed to afford a novel imidazolone derivative (3) containing two ferrocenyl groups. The structures of the products were determined by IR, 1H- and 13C-NMR spectroscopy (including 2D-COSY, DEPT, 2D-HMQC, and 2D-HMBC measurements), and in the case of compound 3 also by single-crystal X-ray analysis.

KW - Ferrocenes

KW - Ferrocenylimidazole derivatives

KW - Iminophosphorane

KW - NMR

KW - Structure elucidation by IR

KW - X-ray

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JF - Journal of Organometallic Chemistry

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