The preparation, spectroscopy, structure and electrochemistry of some [Co(η4-C4Ph4)(η5-C5H4CC–CHY)], [Fe(η5-C5H5)(η5-C5H4CC–CHY)], and related complexes

Courtney, Donagh; McAdam, C. John; Manning, A. R.; Müller‐Bunz, Helge; Ortin, Yannick

doi:10.1016/j.jorganchem.2011.12.012

Cited by 13 publications

(4 citation statements)

References 80 publications

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“…The key precursor 1,1-dibromo-2-ferrocenylethene ( 2 ) is readily prepared from the reaction of ferrocenecarboxaldehyde (Fc-CHO, 1 ) with PPh 3 /CBr 4 (Corey–Fuchs reaction) (Scheme ). , Compound 2 is a versatile precursor of ethynylferrocene, , but despite the wider synthetic versatility of 1,1-dihalovinyl compounds, , other reactions of 2 appear to be limited to the preparation of ferrocene-substituted vinylic dithioethers and heterometallic oxidative addition products …”

Section: Resultsmentioning

confidence: 99%

Syntheses, Spectroelectrochemical Studies, and Molecular and Electronic Structures of Ferrocenyl Ene-diynes

et al. 2013

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Section: Resultsmentioning

confidence: 99%

Syntheses, Spectroelectrochemical Studies, and Molecular and Electronic Structures of Ferrocenyl Ene-diynes

et al. 2013

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“…This was probed by introduction of ethenyl ( 1 f ), ethynyl ( 1 g ) and phenyl ( 1 h ) spacers. Carboxylic acid 1 f was prepared in two steps from readily available ferrocenecarboxaldehyde, [16f] whereas the synthesis of 1 g required an adaptation of literature procedures and was realised in three steps from ferrocenecarboxaldehyde [16a] . Finally, 1 h was obtained by the reaction of ferrocene with 4‐(methoxycarbonyl)benzenediazonium and subsequent saponification of the methyl ester [16g] .…”

Section: Resultsmentioning

confidence: 99%

Heteroleptic Dirhodium(II) Complexes with Redox‐Active Ferrocenyl Ligands: Synthesis, Electrochemical Properties, and Redox‐Responsive Chemoselectivity in Carbene C−H Insertion

et al. 2022

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A series of original heteroleptic dirhodium(II) complexes (4 a–j) of formula [Rh2(OAc)3(L)], where L is a redox‐active ferrocenecarboxylate ligand, has been prepared. These dirhodium(II) complexes have been characterised by NMR, mass spectrometry and cyclic voltammetry. All complexes show a quasi‐reversible redox behaviour for the ferrocenyl unit. The latter can be selectively oxidised by [N(4‐C6H4Br)3]+BF4−. Four selected heteroleptic complexes 4 a, 4 b, 4 f and 4 i, have been evaluated as catalysts for the intramolecular decomposition of a diazo compound 5. The ratio between the aromatic substitution product 6 and the aliphatic C−H insertion product 7 increases (up to 19 % increase) when using the in situ generated oxidised form of the dirhodium(II) complexes (4 a+BF4− to 4 i+BF4−). This shows that the oxidation of the ferrocenecarboxylate ligand has an effect on the chemoselectivity of the dirhodium‐catalysed diazo decomposition, and thus that the electronic properties of a complex can be tuned without exchanging ligands.

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“…No special precautions were taken to exclude air or moisture during workup except where otherwise indicated. Ethynyl ferrocene (1) was synthesised according to ref [31] or [32]. The compounds 3 [15] The concentrations of the analytes and the supporting electrolyte used in these measurements were 1.3 × 10 -2 and 3 × 10 -1 mol dm -3 for IR, and 10 -3 and 3 × 10 -1 mol dm -3 for the UV-vis-NIR studies, respectively.…”

Section: General Conditionsmentioning

confidence: 99%

Tetrakis(ferrocenylethynyl)ethene: Synthesis, (Spectro)electrochemical and quantum chemical characterisation

Vincent

Gluyas²,

Gückel

et al. 2016

Journal of Organometallic Chemistry

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Tetra(ferrocenylethynyl)ethene (1) has been prepared in four steps from ethynyl ferrocene (2). In a dichloromethane solution containing 10 -1 M NBu 4 PF 6 , only a single oxidation process is observed by cyclic voltammetry, corresponding to the independent oxidation of the four ferrocenyl moieties. However, in dichloromethane containing 10 -1 M NBu 4 BAr F 4 electrolyte, where [BAr F 4 ]is the weakly associating anion [B{C 6 H 3 (CF 3 ) 2 -3,5}] -, four distinct oxidation processes are resolved, although further spectroelectrochemical investigation revealed essentially no through bond interaction between the individual ferrocene moieties. Quantum chemical treatment of 1 identified several energetic minima corresponding to different relative orientations of the ferrocene moieties and the plane of the all-carbon bridging fragment. Further computational investigation of the corresponding monocation [1] + supported the notion of charge localisation with no evidence for significant through bond electronic interactions.

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The preparation, spectroscopy, structure and electrochemistry of some [Co(η4-C4Ph4)(η5-C5H4CC–CHY)], [Fe(η5-C5H5)(η5-C5H4CC–CHY)], and related complexes

Cited by 13 publications

References 80 publications

Syntheses, Spectroelectrochemical Studies, and Molecular and Electronic Structures of Ferrocenyl Ene-diynes

Syntheses, Spectroelectrochemical Studies, and Molecular and Electronic Structures of Ferrocenyl Ene-diynes

Heteroleptic Dirhodium(II) Complexes with Redox‐Active Ferrocenyl Ligands: Synthesis, Electrochemical Properties, and Redox‐Responsive Chemoselectivity in Carbene C−H Insertion

Tetrakis(ferrocenylethynyl)ethene: Synthesis, (Spectro)electrochemical and quantum chemical characterisation

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