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Synthesis and Structure of Geometric Isomers of 1-[(methoxyimino)ethyl]-ferrocene and Methyl 1'-[(methoxyimino)ethyl]ferrocene-1-carboxylate

Mojca Čakić Semenčić ; Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottijeva 6, HR-10000 Zagreb, Croatia
Gordana Pavlović   ORCID icon orcid.org/0000-0002-2317-3348 ; Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, HR-10000 Zagreb, Croatia
Dubravka Šišak ; ETH- Zürich, Department of Materials, Laboratory for Crystallography, Wolfgang Pauli Strasse 10, CH-8039 Zürich, Switzerland
Vladimir Rapić ; Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottijeva 6, HR-10000 Zagreb, Croatia

Puni tekst: engleski, pdf (3 MB) str. 307-314 preuzimanja: 1.172* citiraj
APA 6th Edition
Čakić Semenčić, M., Pavlović, G., Šišak, D. i Rapić, V. (2010). Synthesis and Structure of Geometric Isomers of 1-[(methoxyimino)ethyl]-ferrocene and Methyl 1'-[(methoxyimino)ethyl]ferrocene-1-carboxylate. Croatica Chemica Acta, 83 (3), 307-314. Preuzeto s https://hrcak.srce.hr/62208
MLA 8th Edition
Čakić Semenčić, Mojca, et al. "Synthesis and Structure of Geometric Isomers of 1-[(methoxyimino)ethyl]-ferrocene and Methyl 1'-[(methoxyimino)ethyl]ferrocene-1-carboxylate." Croatica Chemica Acta, vol. 83, br. 3, 2010, str. 307-314. https://hrcak.srce.hr/62208. Citirano 07.12.2019.
Chicago 17th Edition
Čakić Semenčić, Mojca, Gordana Pavlović, Dubravka Šišak i Vladimir Rapić. "Synthesis and Structure of Geometric Isomers of 1-[(methoxyimino)ethyl]-ferrocene and Methyl 1'-[(methoxyimino)ethyl]ferrocene-1-carboxylate." Croatica Chemica Acta 83, br. 3 (2010): 307-314. https://hrcak.srce.hr/62208
Harvard
Čakić Semenčić, M., et al. (2010). 'Synthesis and Structure of Geometric Isomers of 1-[(methoxyimino)ethyl]-ferrocene and Methyl 1'-[(methoxyimino)ethyl]ferrocene-1-carboxylate', Croatica Chemica Acta, 83(3), str. 307-314. Preuzeto s: https://hrcak.srce.hr/62208 (Datum pristupa: 07.12.2019.)
Vancouver
Čakić Semenčić M, Pavlović G, Šišak D, Rapić V. Synthesis and Structure of Geometric Isomers of 1-[(methoxyimino)ethyl]-ferrocene and Methyl 1'-[(methoxyimino)ethyl]ferrocene-1-carboxylate. Croatica Chemica Acta [Internet]. 2010 [pristupljeno 07.12.2019.];83(3):307-314. Dostupno na: https://hrcak.srce.hr/62208
IEEE
M. Čakić Semenčić, G. Pavlović, D. Šišak i V. Rapić, "Synthesis and Structure of Geometric Isomers of 1-[(methoxyimino)ethyl]-ferrocene and Methyl 1'-[(methoxyimino)ethyl]ferrocene-1-carboxylate", Croatica Chemica Acta, vol.83, br. 3, str. 307-314, 2010. [Online]. Dostupno na: https://hrcak.srce.hr/62208. [Citirano: 07.12.2019.]

Sažetak
Here we report synthesis, spectral data and single-crystal X-ray molecular and crystal structures
of (E)-1-[(methoxyimino)ethyl] ferrocene (2) and (E)-methyl 1'-[(methoxyimino)ethyl]ferrocene-1-
carboxylate (4). These organometallics are recognized as precursors for optically pure (1-
ferrocenylethyl)amine (Fea) and 1'-(1-aminoethyl)ferrocene-1-carboxylic acid (Fcca) derivatives. The
(E/Z)mixtures of the title compounds 2 and 4 were obtained in ≈90 % yield by the action of methoxyamine
hydrochloride on acetylferrocene (1) and 1'-acetylferrocene-1-carboxylic acid (3). By means of preparative
thin layer chromatography the synthesized compounds were separated into 75 % of (E)-2 and 15
% of (Z)-2, as well as into 68 % of (E)-4 and 22 % of (Z)-4.
Crystal structures of the dominant isomers of 2 (two molecules within asymmetric unit) and 4 confirm
that both compounds exist in (E)-forms. The ferrocenyl moieties deviate slightly from eclipsed conformation
in 2 and 4. The intramolecular C−H···O contact in the C(CH3)−N−OCH3 group (2.670(7) Å in the
second molecule of 2 and 2.644(6) Å in 4) can be regarded as a weak intramolecular hydrogen bond. The
crystal packings of 2 and 4 are characterized only by van der Waals forces.

Ključne riječi
[(methoxyimino)ethyl]ferrocene derivatives; E/Z isomerism; synthesis; crystal structure

Hrčak ID: 62208

URI
https://hrcak.srce.hr/62208

Posjeta: 1.419 *