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Unexpected formation of novel benzofuranyl-substituted ferrocenes by action of p-benzoquinone on 1,1′-bis-acylferrocene

A Michael addition was found to occur between 1,1′-bis-(undecanoyl)ferrocene and p-benzoquinone in the presence of tetrafluoroboric acid leading to the formation of benzofuranyl ferrocene derivatives.Under similar conditions, the fluoroalkyl 1,1′-bis<11-(F-octyl)-undecanoyl>ferrocene and the acetylferrocene analogue are oxidized to their respective ferricinium ions.

Unexpected formation of novel benzofuranyl-substituted ferrocenes by action of p-benzoquinone on 1,1′-bis-acylferrocene

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
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Selective functionalization of ferrocenyl compounds using a novel solvent free synthetic method for the preparation of bioactive unsymmetrical ferrocenyl derivatives

A novel solvent free synthetic method has been designed by using rice husk ash (RHA) as solid support for the selective functionalization of ferrocenyl derivatives and described the synthesis of a 1,1?-unsymmetrically bi-functionalized ferrocenyl compounds for their biological evaluation. Single crystal X-ray structural evaluation showed some interesting intra-molecular hydrogen bonding interactions across the chains of the ferrocenyl molecule, while DFT calculation revealed the significance of the orientation between the two cyclopentadienyl rings for the hydrogen bonding interaction. Redox and antibacterial properties have been studied to understand the electronic and biological effect of different hydrazone system and their potential for future application.

Selective functionalization of ferrocenyl compounds using a novel solvent free synthetic method for the preparation of bioactive unsymmetrical ferrocenyl derivatives

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Nucleophilic aromatic substitution of 2-(3(5)-pyrazolyl)pyridine: A novel access to multidentate chelate ligands

1-(Nitrophenyl) functionalized 2-(3-pyrazolyl)pyridines were obtained by a nucleophilic aromatic substitution and could be reduced to the corresponding aminophenyl substituted derivatives. These compounds can be used to co-ordinate transition metal sites or for the generation of building blocks for supramolecular chemistry. The solid state structure of a 1,1?- functionalized ferrocene, which was obtained following this route, is discussed in detail.

Nucleophilic aromatic substitution of 2-(3(5)-pyrazolyl)pyridine: A novel access to multidentate chelate ligands

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
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Preparation of ferrocenyl mono- and dienone derivatives through aldol condensation of 1,1?-diacetylferrocene with aromatic aldehydes in dry conditions

1,1?-Diacetylferrocene was condensed with aromatic aldehydes without solvent in the presence of solid NaOH. Diacetylferrocene can give good yields of mono- or diene with either one or two molecules of a wide range of aldehydes depending only on the stoichiometry. Cyclization to ferrocenphane does not occur in this condition.

Preparation of ferrocenyl mono- and dienone derivatives through aldol condensation of 1,1?-diacetylferrocene with aromatic aldehydes in dry conditions

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
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Ferrocene containing N-tosyl hydrazones as optical and electrochemical sensors for Hg2+, Cu2+ and F? ions

Ferrocene containing N-tosyl hydrazones as selective and sensitive optical and electrochemical chemosensors were synthesized and characterized by 1H NMR, 13C NMR, ESI-MS and X-ray analysis. The cation and anion binding studies were carried out using various techniques including electrochemistry, UV?vis and 1H NMR spectroscopy. Chemosensors 2a and 2b have shown excellent selective recognition toward Hg2+, Cu2+ and F? through optical and electrochemical signals. The color of 2a and 2b in solution changed visibly from pale yellow to red upon addition of Hg2+ion, while the color of solution changed from pale yellow to yellow green upon addition of Cu2+, which can be easily detected by the naked eye.

Ferrocene containing N-tosyl hydrazones as optical and electrochemical sensors for Hg2+, Cu2+ and F? ions

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
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In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. In homogeneous catalysis, catalysts are in the same phase as the reactants. name: 1,1′-Diacetylferrocene. Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. Introducing a new discovery about 1273-94-5, Name is 1,1′-Diacetylferrocene

Asymmetric addition of diethylzinc to aromatic aldehydes by chiral ferrocene-based catalysts

A series of chiral C1- and C2-symmetric ferrocenyl Schiff bases (1a-c), ferrocenyl aminoalcohols (2a), ferrocenylphosphinamides (2b-c), 1,1?-ferrocenyl-diol (3), and 1,1?-ferrocenyl-disulfonamide (4) were prepared and employed as base catalysts or as ligand for titanium(IV) complexes in the asymmetric addition of diethylzinc to aromatic aldehydes. High enantioselectivity up to almost 100% ee was achieved for the alkylation of benzaldehyde and p-methoxybenzaldehyde with 1 or 3. In contrast, however, the beta-aminoalcohol (2a) and phosphinamides (2b and c) that are ubiquitous classes of base catalysts for this reaction proved inefficient in our hands, regardless of the types of substrates or reaction conditions. Comparative studies show that there exist various reaction parameters governing not only chemical yields but also optical yields. These include steric and electronic environment of the substrate, the solvent, the reaction temperature, and the nature of the ferrocene moieties.

Asymmetric addition of diethylzinc to aromatic aldehydes by chiral ferrocene-based catalysts

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
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In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. In homogeneous catalysis, catalysts are in the same phase as the reactants. Recommanded Product: 1,1′-Diacetylferrocene. Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. Introducing a new discovery about 1273-94-5, Name is 1,1′-Diacetylferrocene

Intra- and intermolecular charge transfer: Twin themes and simultaneous competing transitions involving ferrocenes

Electronic absorption spectra of ferrocene, ferrocenecarboxylaldehyde, butylferrocene, and 1,1?-diacetylferrocene in pure organic polar and non-polar solvents, pure halocarbon solvents and in several hexane-halocarbon solvent mixtures have been recorded. The investigated ferrocenes have shown several intra-molecular electronic transitions of the types pi-pi*, n-pi*, and d-d*. On using protonic solvents (HA) each of the ferocenes (Fc) acquires a proton exported from the solvent to form a complex with the formula [FcH]+[A]-. However, on using halocarbon solvents each of the ferrocenes has shown an intermolecular charge-transfer-to-solvent (CTTS) which is characterized by the appearance of new absorption spectral band(s) for each ferrocene-halocarbon solvent interaction. Formation constants (KCT) and molar absorption coefficients (epsilonCT) of these interactions have been determined and discussed. The study has indicated that the observed different transitions are dependent upon the number and nature of the substituents involved in the ferrocenes.

Intra- and intermolecular charge transfer: Twin themes and simultaneous competing transitions involving ferrocenes

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
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Conformation-switched chemosensor for selective detection of Hg2+ in aqueous media

A conformation flexible chemosensor for selective detection of Hg2+ in aqueous media was achieved by incorporating two well-known rhodamine-6G dyes and a ferrocene group within one molecule. Distinguished from the monosubstituted ferrocene derivative which is previously reported a lack of interaction with Hg2+, the title compound was characteristic of two-armed bidendate binding unit. The Hg2+ sensing behavior can be switched via the conformation flexibility. The 1:1 sensor/Hg2+ binding mode was proposed and supported by the titration experiment and ESI mass spectrum. The fluorescent sensor can display a highly selective response of fluorescence enhancement toward Hg2+ and detect the parts per billion (ppb) level of Hg2+ in aqueous environment. Crown Copyright

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1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquids as solvents for Friedel-Crafts acylation reactions of ferrocene

Friedel-Crafts acylations of ferrocene in 1-ethyl-3-methylimidazolium halogenoaluminate ionic liquids, [emim]I-(AlCl3)x are described.3 The effect of varying the “bulk” Lewis acidity of the ionic liquids used as solvents in these reactions and the effect of varying the relative amounts of acylating agent with respect to the amount of ferrocene in these reactions is also described. The use of a variety of different acylating agents in our studies demonstrates the scope of this reaction performed in these ionic liquid systems.

1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquids as solvents for Friedel-Crafts acylation reactions of ferrocene

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Conformational analysis of the [(C5H4CR?R?)2m]2+ dications (M = Ru, Os) as a tool for determining their onium or dicarbocation structure

The [(Me2CC5H4)2M]2+ and [(Me(H)CC5H4)2M]2+ dications (M = Ru, Os) were generated and their precursors, dicarbinols, were synthesized. 1H NMR spectral analysis showed that the former dications have a dicarbocation structure. For the [(Me(H)CC5H4)2M]2+ dications, the energies of both the onium and dicarbocation structures are close, and compounds of both types can be simultaneously observed in solution.

Conformational analysis of the [(C5H4CR?R?)2m]2+ dications (M = Ru, Os) as a tool for determining their onium or dicarbocation structure

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion