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N-tert-Alkyl-Substituted N-Heterocyclic Carbenes with a 1,1’-Ferrocenediyl Backbone

dc.date.accessioned2022-04-19T11:04:29Z
dc.date.available2022-04-19T11:04:29Z
dc.date.issued2021-12-14
dc.identifierdoi:10.17170/kobra-202203035826
dc.identifier.urihttp://hdl.handle.net/123456789/13762
dc.description.sponsorshipGefördert im Rahmen des Projekts DEALger
dc.language.isoengeng
dc.rightsNamensnennung 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectamineseng
dc.subjectcarbeneseng
dc.subjectironeng
dc.subjectmetalloceneseng
dc.subjectx-ray diffractioneng
dc.subject.ddc540
dc.titleN-tert-Alkyl-Substituted N-Heterocyclic Carbenes with a 1,1’-Ferrocenediyl Backboneeng
dc.typeAufsatz
dcterms.abstract1,1’-Diaminoferrocene (1) was converted to α-aminonitriles fc[NHC(CN)MeR’]₂ (fc=1,1’-ferrocenediyl; 2 a: R’=Me, 2 b: R’=Ph, 2 c: R’=tBu) by reaction with ketones MeC(O)R’ in the presence of NaCN/HOAc or to the diimine fc(N=CPh₂)₂ (3) by condensation with Ph₂CO. Treatment of 2 a–c or 3 with MeLi furnished fc(NHR)₂ (4 a: R=tBu, 4 b: R=CMe₂Ph, 4 c: R=CMe₂tBu, 4 d: R=CMePh₂) after aqueous work-up. The formylative cyclisation of 4 a–d to fc[(NR)₂CH][BF₄] (5H[BF₄]) was possible only for R=CMe₃ (a) and CMe₂Ph (b). The reaction of these formamidinium compounds with NaN(SiMe₃)₂ afforded the N-heterocyclic carbenes fc{[N(CMe₃)]₂C:} (5 a) and fc{[N(CMe₂Ph)]₂C:} (5 b). 5 a was converted to the thiourea derivative 5 aS with elemental sulfur. 5 a and 5 b slowly decompose in solution by alkene elimination, affording the respective formamidine fc(NRCH=N) (6 a: R=CMe₃, 6 b: R=CMe₂Ph). 6 a was transformed to fc{[N(CMe₃)][N(CPh₃)]CH}[BF₄] (5eH[BF₄]) with Ph₃C[BF₄].eng
dcterms.accessRightsopen access
dcterms.creatorCorreia Bicho, Bruno Alexandre
dcterms.creatorGuthardt, Robin
dcterms.creatorBruhn, Clemens
dcterms.creatorGroßhenning, David
dcterms.creatorOrth, Till
dcterms.creatorPfeiffer, Florian
dcterms.creatorSiemeling, Ulrich
dc.relation.doidoi:10.1002/ejic.202101014
dc.subject.swdAmineger
dc.subject.swdCarbeneger
dc.subject.swdEisenger
dc.subject.swdMetalloceneger
dc.subject.swdRöntgenbeugungger
dc.type.versionpublishedVersion
dcterms.source.identifiereissn:1099-0682
dcterms.source.issueIssue 7
dcterms.source.journalEurJIC (European Journal of Inorganic Chemistry)eng
dcterms.source.volumeVolume 2022
kup.iskupfalse
dcterms.source.articlenumbere20210114


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Namensnennung 4.0 International
Except where otherwise noted, this item's license is described as Namensnennung 4.0 International