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Related Products of 12180-80-2, hemistry, like all the natural sciences, begins with the direct observation of nature— in this case, of matter. In a document type is Article, molecular formula is C24H10FeO2, molecular weight is 386.18, and a compound is mentioned, 12180-80-2, 1,1′-Dibenzoylferrocene, introducing its new discovery.

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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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

 

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A reaction between cyclopentadienylsodium and ethyl benzoate in refluxing THF produces (benzoylcyclopentadienyl)sodium (4) in 70-80percent yield.Subsequent treatment of 4 in ethanol solution with thallium ethoxide affords (benzoylcyclopentadienyl)thallium (3) in nearly quantitative yield.Reactions of 3 with Mn(CO)5Br, Re(CO)5Br, 2 or FeCl2 lead to the respective eta5-benzoylcyclopentadienyl derivatives of these metals, and demonstrate the utility of 3 in organometallic syntheses.Reactions of several of these organometallic ketones with cymantrenyllithium<(eta5-C5H4Li)Mn(CO)3> provide a useful new route to bimetallic compounds.

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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

 

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1,1′-Dibenzoylferrocene reacts with tetraphosphorus decasulphide to yield, in addition to the expected 1,1′-bis(thiobenzoyl)ferrocene, a minor, yellow by-product (1) of composition C24H18FeS3.Crystals of (1) are monoclinic, space group P21/n with a = 11.769(3), b = 11.750(4), c = 14.835(2) Angstroem, beta = 98.63(1) deg, and Z = 4; the structure was refined from diffractometer data to an R value of 0.041.The structure was found to be that of 1,4-diphenyl-1,4-epithio-2,3-dithia<4>(1,1′)ferrocenophane, in which the two rings of the ferrocene nucleus are spanned by a 1,2,4-trithiolane ring.

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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

 

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In (1?-benzoylferrocenyl)diphenylmethanol, [(PhCO-C5H4)Fe(C5H4)]CPh 2OH (C30H24FeO2), there is an intramolecular O-H…O hydrogen bond with O…O 2.891 (2) A; the ferrocenyl unit adopts an eclipsed conformation and the molecules are linked into centrosymmetric dimers by C-H…O hydrogen bonds with C…O 3.357 (3) A, to generate a cyclic R44(16) motif.

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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

 

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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. Computed Properties of C24H10FeO2. Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. Introducing a new discovery about 12180-80-2, Name is 1,1′-Dibenzoylferrocene

Ferrocenes bearing acyl substituents in the cyclopentadienyl rings [Fe(eta5-C5H4COR)(eta5-C 5H5)] and [Fe(eta5-C5H 4COR)2] (R = CH3, CF3 and Ph) were examined as new driers for solvent-borne alkyd binder. All studied ferrocenes were found to be active catalysts for cross-linking reaction of the alkyd. These iron(II) compounds give solid polymeric films with hardness and drying time comparable to the commercial cobalt(II) drier. Acetyl- and benzoyl-substituted ferrocenes show an excellent synergic effect with the cobalt drier giving hard polymeric films within short drying time. The kinetics of the alkyd autoxidation was followed by FTIR spectroscopy. Spin-trapping ESR technique has proven the important role of the ferrocenium cation upon decomposition of hydroperoxides by ferrocene-based driers. The peroxy and alkoxy radicals, appearing in drying process, were resolved by the new spin trap methyl-N-mesityl nitrone.

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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

 

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The syntheses and characterization of heterodi- and heterotrimetallic complexes of general formulas [Pd{[(eta5-C5H 3)-C(R)=N-R?]Fe[(eta5-C5H 4)-C(R)=N-R?]}Cl(PPh3)] [Pd{[(eta5-C5H3)C(C6H 5)=N-C6H5]Fe[(eta5-C 5H4)-C(O)=N-C6H5]}Cl(PPh 3)], and [Pd2{Fe[(eta5-C5H3)-C(R)= N-R?]2}Cl2(PPh3)2] {with R = H, CH3, or C6H5 and R?= phenyl or benzyl groups} are reported. The X-ray crystal structure of the meso-form of [Pd2{Fe[(eta5-C5H3)-C(CH 3)=N-C6H5]2}Cl2(PPh 3)2] (2b) is also described.

heterodi- and heterotrimetallic compounds containing five-membered rings and sigma(Pd-Csp2, ferrocene) bonds. X-ray crystal structure of the meso-form of [Pd2{Fe[(eta5-C5H3)-C(CH 3)=N-C6H5]}2Cl2(PPh 3)2]

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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

 

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The synthesis and mercuration of a series of Schiff bases 1?-benzoyl-1-[(arylimino)phenylmethyl]ferrocene (aryl: a variety of substituted phenyls) have been studied. In all cases the mercuration occurred at the 2-position of the ferrocene ring. Oxygen ? mercury coordinated products were not obtained. The X-ray crystal structure of [2-chloromercurio-1-[((phenylimino)phenylmethyl)-1?-benzoyl] ferrocene 5c has been determined; this crystallizes in the monoclinic, space group P21/c with a =10.168(3), b= 16.105(3), c = 15,463(4)A, beta = 103.61(2) and Z = 4. Refinement of atomic parameters gave an R factor of 0.038 (Romega = 0.055) for 2440 unique reflections having 1>3sigma(1). The structure confirms the formation of a five-membered metallocycle on the ferrocene moiety.

Cyclometallation of ferrocenylimines III. Regioselectivity in Hg(II) cyclometallated complexes

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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

 

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A series of mono- and 1,1′-diheteroatom-substituted ferrocene derivatives as well as acylated ferrocenes was prepared efficiently by a unified strategy that consists of selective mono- and 1,1′-dilithiation reactions and subsequent coupling with carbon, phosphorus, sulfur and halogen electrophiles. Chemical oxidation of the ferrocene derivatives by benzoquinone, 2,3-dichloro-5,6- dicyanobenzoquinone, AgPF6, or 2,2,6,6-tetramethyl-1-oxopiperidinium hexafluorophosphate provided the corresponding ferrocenium salts. The redox potentials of the synthesized ferrocenes were determined by cyclic voltammetry, and it was observed that all new ferrocenium salts have stronger oxidizing properties than standard ferrocenium hexafluorophosphate. An initial application of selected derivatives in an oxidative bicyclization revealed that they mediate the transformation under considerably milder conditions than ferrocenium hexafluorophosphate. Quantum chemical calculations of the reduction potentials of the substituted ferrocenium ions were carried out by using a standard thermodynamic cycle that involved the gas-phase energetics and solvation energies of the contributing species. A remarkable agreement between theory and experiment was found: the mean average deviation amounted to only 0.030-V and the maximum deviation to 0.1-V. This enabled the analysis of various physical contributions to the computed reduction potentials of these ferrocene derivatives, thereby providing insight into their electronic structure and physicochemical properties. Copyright

Acceptor-substituted ferrocenium salts as strong, single-electron oxidants: Synthesis, electrochemistry, theoretical investigations, and initial synthetic application

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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

 

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Ruthenium-Catalyzed Enantioselective Hydrogenation of Ferrocenyl Ketones: A Synthetic Method for Chiral Ferrocenyl Alcohols

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.

Ruthenium-Catalyzed Enantioselective Hydrogenation of Ferrocenyl Ketones: A Synthetic Method for Chiral Ferrocenyl Alcohols

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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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Studies on the cyclomercuration of 1,1?-bis[(arylimino)phenylmethyl]ferrocenes

The reaction of bisferrocenylimines with mercuric acetate and subsequent treatment with LiCl lead to formation of mono (9) and double (10) cyclomercurated derivatives. The 1H NMR and 199Hg NMR spectra of the double cyclomercurated bisferrocenylimines show that compounds 10 exist as two isomers (meso and dl). The individual stereoisomers were isolated successfully by crystal picking. The structures of these new compounds have been confirmed by elemental analysis, IR and 1H NMR spectroscopies, and further by X-ray crystal structure determination of meso [{HgCl(eta5-C5H3CPh=NAr)}2Fe] (Ar=m-CH3C6H4).

Studies on the cyclomercuration of 1,1?-bis[(arylimino)phenylmethyl]ferrocenes

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Reference£º
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