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The structure of protonated ferrocenes has been investigated using 1H NMR and 57Fe Moessbauer spectroscopy.The ketones were fully protonated in CF3CO2H and in 70percent H2SO4/H2O.In more concentrated sulphuric acid < > 90percent H2SO4/H2O) rapid heteroannular sulphonation occurred.No evidence was obtained of any iron protonation in these systems.For the para substituted aromatic derivatives C5H5FeC5H4COC6H4X the NMR data indicates steric inhibition to resonance. 1,1′-Diketones are doubly protonated in strongly acid media (98percent H2SO4, CF3SO3H).Moessbauer data on the solid ketones showed decrease in quadrupole splitting (QS), relative to ferrocene itself, of about 0.12 mm s-1 for each successive acyl function added.For solid solutions of the protonated ketones in CF3CO2H this decrease (DeltaQS) was much larger at about 0.28 mm s-1.The results are interpreted as involving electron withdrawal from ring-based orbitals (epsilon1), rather than the iron-based orbitals (epsilon2).In the aromatic series, DeltaQS was significantly smaller for electron withdrawing substituents.

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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

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A […] of highly dilute preparation method, comprises the following steps: step 1), in the added into the dry CH […] in2 Cl2 , Pyridine and aniline derivatives stirring after; step 2), non-water treated CH2Cl2 dissolved 1, 1′ – ferrocene dicarboxylic acyl chloride, to slowly dropping in the […], after dropping the first reaction is carried out at room temperature, then slow heating, reflux; monitoring the reaction process for thin plate and, when one of the raw material point disappears, stopping the reaction; step 3), evaporate solution in dichloromethane, residual liquid water washing several times, the collected organic phase with anhydrous MgSO4 After drying the solvent evaporate under reduced pressure, then to admix the residual liquid in the silica gel, eluting agent selected: VPetroleum ether : VAcetic acid ethyl ester =3:1 elution, column purification, to obtain a final […]. The invention can simplify the link flourishing synthetic process, improve its productive rate with the fluorescence intensity, save the process cost. (by machine translation)

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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

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Acetyl ferrocene and diacetyl ferrocene both readily react with an excess of hydrazine to afford the corresponding hydrazone compounds. These compounds can then be linked to Re(CO)3 via a metal-mediated Schiff base reaction, resulting in a series of ferrocene-Re(CO)3 conjugates with different stoichiometries. Conjugates with 1:1, 1:2, and 2:1 ferrocene: Re(CO)3 ratios can be produced via this “modular” type synthesis approach. Several examples of these conjugates were structurally characterized, and their spectroscopic, electrochemical, and spectroelectrochemical behaviors were investigated. The electronic structures of these compounds were also probed using DFT and TDDFT calculations.

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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

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57Fe NMR spectra of 20 ferrocene derivatives with natural abundance of 57Fe have been recorded by the conventional pulse Fourier transform technique using ferrocene as internal standard for the chemical shifts.Shift contributions of the substituents are discussed qualitatively.

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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

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The Clemmensen reduction of a carbonyl group to give, in the simplest cases, a methylene unit, is one of the more familiar reactions in organic chemistry. Trimethylchlorosilane as a replacement for the proton allows controlled reductive deoxygenation of carbonyl compounds under formally anhydrous conditions as an alternative to the McMurry dicarbonyl coupling reaction. Aromatic carbonyl compounds with electron-donor substituents are preferred substrates for this reaction to yield symmetrical olefins in good yield. The high donor capacity of metallocenyl groups should especially favor the clean formation of olefins from the corresponding metallocenyl ketones. In this study, a number of ferrocenyl and ruthenocenyl aldehydes and ketones were treated with Zn and trimethylchlorosilane under controlled anhydrous reaction conditions with (a) catalytical and (b) low amounts of H+ present. The observed main products include alkanes, alkenes, silylated pinacols, and rearranged pinacolones, which have been characterized by spectroscopic methods and by X-ray analyses. The diverse outcome in these reactions indicates a reaction mechanism which involves electrophilic catalysis with different energetically similar pathways.

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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

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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.

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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

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Mono-and disubstituted ferrocenes react with excess mercuric acetate (at least eight or nine equivalents) to afford highly insoluble mixtures of polymercurated ferrocenes. In the case of 1,1?-dimethylferrocene, the mercurated product is composed of minor amounts of the octamercurated and hexamercurated ferrocenes, with the heptamercurated ferrocene being the major product. This analysis is based upon results of chlorination and bromination studies of the mercurated species. It is proposed that exhaustive mercuration fails due to the extreme insolubility of the higher mercurated products.

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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

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Since oxidation and reduction reactions mainly take place on surfaces, enlarging the specific surface of redox materials is the key to achieving excellent electrochemical performance. In this work, by using silica monolayer colloidal crystal templates (MCCTs), a nanostructured Fc(COCH3)2 film is prepared successfully, and such a nanostructure could exhibit the following unique electrochemical properties: the MCCTs could impede the aggregation tendency of Fc(COCH3)2 and possess high electrochemical activity; Fc(COCH3)2 enlarges the contact area and offers more active sites and faster electronic transmission channels. The structure, optical and electrochemical properties of the nanostructured Fc(COCH3)2 were tested and then compared with those of compact Fc(COCH3)2 films to evaluate the role of the nanoarchitecture. The unique structure design of the Fc(COCH3)2 film enables outstanding performance, showing a large transmittance change (DeltaT) of 37% at 550 nm when switched between 0.5 V and -2.5 V, which is approximately ninefold higher than that of the compact Fc(COCH3)2 film (approximately 4%). Response times of coloration and bleaching are found to be only 16.15 s and 5.56 s. Furthermore, the nanostructured Fc(COCH3)2 film shows much better cycling stability than the compact one. The results indicate that the nanostructure could significantly improve the electrochemical performance of the Fc(COCH3)2 film due to the increase in electrochemical active sites and the enhancement of the “D-to-A” redox switch of ferrocene.

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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

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Highly effective asymmetric hydrogenation of various ferrocenyl ketones, including aliphatic ferrocenyl ketones as well as the more challenging aryl ferrocenyl ketones, was realized in the presence of a Ru/diphosphine/diamine bifunctional catalytic system. Excellent enantioselectivities (up to 99.8% ee) and activities (S/C = 5000) could be obtained. These asymmetric hydrogenations provided a convenient and efficient synthetic method for chiral ferrocenyl alcohols, which are key intermediates for a variety of chiral ferrocenyl ligands and resolving reagents.

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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

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Some novel symmetrically 1,1?-disubstituted ferrocene-derived compounds have been prepared and used as potential ligands for the preparation of Co(II), Cu(II), Ni(II) and Zn(II) metal chelates. The synthesized compounds have been characterized by physical, spectral and analytical data. Screening of these derivatives against pathogenic bacterial species such as Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumoniae, revealed them to possess bactericidal activity.

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Reference：
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