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dc.contributor.author
Čakić Semenčića, Mojca
dc.contributor.author
Pavlovićb, Gordana
dc.contributor.author
Šišak, Dubravka
dc.contributor.author
Rapića, Vladimir
dc.date.accessioned
2019-10-30T09:56:11Z
dc.date.available
2017-06-09T08:24:37Z
dc.date.available
2019-10-30T09:56:11Z
dc.date.issued
2010
dc.identifier.issn
0011-1643
dc.identifier.issn
1334-417X
dc.identifier.uri
http://hdl.handle.net/20.500.11850/27305
dc.identifier.doi
10.3929/ethz-b-000027305
dc.description.abstract
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.
en_US
dc.format
application/pdf
en_US
dc.language.iso
en
en_US
dc.publisher
Croatian Chemical Society
en_US
dc.rights.uri
http://creativecommons.org/licenses/by/3.0/
dc.subject
[(methoxyimino)ethyl]ferrocene derivatives
en_US
dc.subject
E/Z isomerism
en_US
dc.subject
synthesis
en_US
dc.subject
crystal structure
en_US
dc.title
Synthesis and Structure of Geometric Isomers of 1-[(methoxyimino)ethyl]- ferrocene and Methyl 1'-[(methoxyimino)ethyl]ferrocene-1-carboxylate
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution 3.0 Unported
ethz.journal.title
Croatica Chemica Acta
ethz.journal.volume
83
en_US
ethz.journal.issue
3
en_US
ethz.journal.abbreviated
Croat. chem. acta
ethz.pages.start
307
en_US
ethz.pages.end
314
en_US
ethz.version.deposit
publishedVersion
en_US
ethz.identifier.nebis
000032628
ethz.publication.place
Zagreb
en_US
ethz.publication.status
published
en_US
ethz.leitzahl
03401 - Steurer, Walter
en_US
ethz.leitzahl.certified
03401 - Steurer, Walter
ethz.identifier.url
https://hrcak.srce.hr/62208
ethz.date.deposited
2017-06-09T08:24:52Z
ethz.source
ECIT
ethz.identifier.importid
imp59364d77454d645707
ethz.ecitpid
pub:46113
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2017-07-14T20:19:27Z
ethz.rosetta.lastUpdated
2019-10-30T09:56:25Z
ethz.rosetta.versionExported
true
ethz.COinS
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