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 |
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Authors: | Antal Csá mpai,Veronika Kudar,Heinrich Wamhoff |
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Affiliation: | a Research Group for Structural Chemistry and Spectroscopy, Hungarian Academy of Sciences - Department of General and Inorganic Chemistry, Eötvös Loránd University, P.O. Box 32, H-1518 Budapest, Hungary b Kekulé Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk Str. 1, D-53121 Bonn, Germany |
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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. |
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Keywords: | Ferrocene Pyridazine Phase transfer reaction Ring closing metathesis π-Stacking X-ray diffraction |
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