Synthesis, NMR, IR spectroscopic and X-ray study of novel [pyridazin-3(2H)-one-6-yl]ferrocenes and related ferrocenophane derivatives. Study on ferrocenes. Part 14

A. Csámpai, Árvácska Abrán, Veronika Kudar, György Túrós, Heinrich Wamhoff, P. Sohár

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

On treatment with glyoxylic acid and hydrazine hydrate, 1,1′-diacetylferrocene was converted into the separable mixture of 1,1′-bis [pyridazin-3(2H)-one-6-yl]ferrocene and the hydrazone as well as the azine of 1-acetyl-1′-[pyridazin-3(2H)-one-6-yl]ferrocene. Successful cyclizations of 1,1′-bis[pyridazin-3(2H)-one-6-yl]ferrocene resulting in a series of novel ferrocenophanes containing heterocyclic units were performed under phase transfer- and homogeneous catalytic (RCM) conditions by the application of versatile dialkylating agents and second generation Grubbs' catalyst, respectively. The structures were determined by mass spectrometry, IR, 1H and 13C NMR spectroscopy including 2D-COSY, HMQC and HMBC measurements. The solid phase structure of a dimer product with π-stacking interaction was revealed by X-ray analysis.

Original languageEnglish
Pages (from-to)802-810
Number of pages9
JournalJournal of Organometallic Chemistry
Volume690
Issue number3
DOIs
Publication statusPublished - Jan 28 2005

Fingerprint

ferrocenes
azines
hydrazones
Hydrazine
Cyclization
X ray analysis
hydrazines
Phase structure
Hydrates
hydrates
Dimers
Nuclear magnetic resonance spectroscopy
Mass spectrometry
solid phases
mass spectroscopy
hydrazine
dimers
Nuclear magnetic resonance
X-Rays
Derivatives

Keywords

  • π-Stacking
  • Ferrocene
  • Phase transfer reaction
  • Pyridazine
  • Ring closing metathesis
  • X-ray diffraction

ASJC Scopus subject areas

  • Chemical Engineering (miscellaneous)
  • Materials Science (miscellaneous)
  • Materials Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Biochemistry

Cite this

Synthesis, NMR, IR spectroscopic and X-ray study of novel [pyridazin-3(2H)-one-6-yl]ferrocenes and related ferrocenophane derivatives. Study on ferrocenes. Part 14. / Csámpai, A.; Abrán, Árvácska; Kudar, Veronika; Túrós, György; Wamhoff, Heinrich; Sohár, P.

In: Journal of Organometallic Chemistry, Vol. 690, No. 3, 28.01.2005, p. 802-810.

Research output: Contribution to journalArticle

@article{826f3bec759347b883b99d2f5e3d3138,
title = "Synthesis, NMR, IR spectroscopic and X-ray study of novel [pyridazin-3(2H)-one-6-yl]ferrocenes and related ferrocenophane derivatives. Study on ferrocenes. Part 14",
abstract = "On treatment with glyoxylic acid and hydrazine hydrate, 1,1′-diacetylferrocene was converted into the separable mixture of 1,1′-bis [pyridazin-3(2H)-one-6-yl]ferrocene and the hydrazone as well as the azine of 1-acetyl-1′-[pyridazin-3(2H)-one-6-yl]ferrocene. Successful cyclizations of 1,1′-bis[pyridazin-3(2H)-one-6-yl]ferrocene resulting in a series of novel ferrocenophanes containing heterocyclic units were performed under phase transfer- and homogeneous catalytic (RCM) conditions by the application of versatile dialkylating agents and second generation Grubbs' catalyst, respectively. The structures were determined by mass spectrometry, IR, 1H and 13C NMR spectroscopy including 2D-COSY, HMQC and HMBC measurements. The solid phase structure of a dimer product with π-stacking interaction was revealed by X-ray analysis.",
keywords = "π-Stacking, Ferrocene, Phase transfer reaction, Pyridazine, Ring closing metathesis, X-ray diffraction",
author = "A. Cs{\'a}mpai and {\'A}rv{\'a}cska Abr{\'a}n and Veronika Kudar and Gy{\"o}rgy T{\'u}r{\'o}s and Heinrich Wamhoff and P. Soh{\'a}r",
year = "2005",
month = "1",
day = "28",
doi = "10.1016/j.jorganchem.2004.09.086",
language = "English",
volume = "690",
pages = "802--810",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",
number = "3",

}

TY - JOUR

T1 - Synthesis, NMR, IR spectroscopic and X-ray study of novel [pyridazin-3(2H)-one-6-yl]ferrocenes and related ferrocenophane derivatives. Study on ferrocenes. Part 14

AU - Csámpai, A.

AU - Abrán, Árvácska

AU - Kudar, Veronika

AU - Túrós, György

AU - Wamhoff, Heinrich

AU - Sohár, P.

PY - 2005/1/28

Y1 - 2005/1/28

N2 - On treatment with glyoxylic acid and hydrazine hydrate, 1,1′-diacetylferrocene was converted into the separable mixture of 1,1′-bis [pyridazin-3(2H)-one-6-yl]ferrocene and the hydrazone as well as the azine of 1-acetyl-1′-[pyridazin-3(2H)-one-6-yl]ferrocene. Successful cyclizations of 1,1′-bis[pyridazin-3(2H)-one-6-yl]ferrocene resulting in a series of novel ferrocenophanes containing heterocyclic units were performed under phase transfer- and homogeneous catalytic (RCM) conditions by the application of versatile dialkylating agents and second generation Grubbs' catalyst, respectively. The structures were determined by mass spectrometry, IR, 1H and 13C NMR spectroscopy including 2D-COSY, HMQC and HMBC measurements. The solid phase structure of a dimer product with π-stacking interaction was revealed by X-ray analysis.

AB - On treatment with glyoxylic acid and hydrazine hydrate, 1,1′-diacetylferrocene was converted into the separable mixture of 1,1′-bis [pyridazin-3(2H)-one-6-yl]ferrocene and the hydrazone as well as the azine of 1-acetyl-1′-[pyridazin-3(2H)-one-6-yl]ferrocene. Successful cyclizations of 1,1′-bis[pyridazin-3(2H)-one-6-yl]ferrocene resulting in a series of novel ferrocenophanes containing heterocyclic units were performed under phase transfer- and homogeneous catalytic (RCM) conditions by the application of versatile dialkylating agents and second generation Grubbs' catalyst, respectively. The structures were determined by mass spectrometry, IR, 1H and 13C NMR spectroscopy including 2D-COSY, HMQC and HMBC measurements. The solid phase structure of a dimer product with π-stacking interaction was revealed by X-ray analysis.

KW - π-Stacking

KW - Ferrocene

KW - Phase transfer reaction

KW - Pyridazine

KW - Ring closing metathesis

KW - X-ray diffraction

UR - http://www.scopus.com/inward/record.url?scp=13644276465&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=13644276465&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2004.09.086

DO - 10.1016/j.jorganchem.2004.09.086

M3 - Article

AN - SCOPUS:13644276465

VL - 690

SP - 802

EP - 810

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 3

ER -