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The visible absorption spectra and reduction potentials of 11 ferrocenes containing electron-withdrawing substituents were determined in an N-n-butylpyridinium chloride-aluminum chloride molten salt. When the substituent(s) on the cyclopentadienyl ring(s) of ferrocene were varied, the reduction potential was caused to range over 1.25 V, and the wavelength for maximum absorption of visible light was varied by nearly 200 nm. These changes are greater than have been observed for similar ferrocenes in other nonaqueous solvents. Evidence is presented for specific interactions of particular ferrocenes with the molten salt.

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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 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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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.

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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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In the solid state, molecules of 1,1?-dibenzoylferrocene, [Fe(Cl12H9O)2], (I), are linked to form infinite chains in the [100] direction via (cyclopentadienyl)C – H…O hydrogen bonds [C…O 3.354 (4) A]. In the structure of (4-nitrophenyl)ferrocene, [Fe(C5H5)(C11H8NO2)], (II), there are no C – H-…O hydrogen bonds and molecules are separated by normal van der Waals distances. For earlier determinations see Struchkov [Dokl. Akad. Nauk SSSR (1956), 110, 67-70] for (I) and Roberts et al. [J. Chem. Soc. Dalton Trans. (1988), pp. 1549-1556] for (II).

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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 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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Title full: Synthesis and characterization of 1,1?-bis[(N-methyl-N-phenyl)aminomethyl(ethyl)]ferrocenes. Crystal structures of [Fe{(eta5-C5H4)-C(C6H 5){double bond, long}N-CH2C6H4CH3-4} 2] and 2[Fe{(eta5-C5H4)-CH2N (CH3)-C6H4OCH3-4}2] · 1/4H2O. Direct or catalytic condensation of diacylferrocenes (acyl = formyl, acetyl, and benzoyl) and anilines or benzylamines with titanium tetrachloride as a catalyst resulted in the corresponding diimines 1-3, respectively. Reduction of these imines with sodium borohydride or lithium aluminum hydride/aluminum chloride in THF yielded 1,1?-bis[(N-phenyl)aminomethyl(ethyl)]ferrocenes (4, 5) and 1,1?-bis[(N-benzyl)aminobenzyl]ferrocenes (6), respectively. Reductive methylation of 4-6 with aqueous formaldehyde, cyanoborohydride and acetic acid only afforded 1,1?-bis[(N-methyl-N-phenyl)aminomethyl(ethyl)]ferrocenes (7, 8). 1,1?-Bis[{(N-methyl-N-benzyl)amino}benzyl]ferrocenes (9) were not obtained, probably due to their debenzylation under the acidic conditions. The molecular structures of 3g and 7a were determined by single crystal X-ray analysis.

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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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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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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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An efficient and flexible asymmetric synthesis of planar chiral 2-mono- and 2,2?-disubstituted 1,1?-bisbenzoylferrocenes 4 and 6 is reported. Key step is a highly diastereoselective ortho-metalation of 1,1?-bisbenzoylferrocene 1 via the corresponding bis-SAMP-hydrazone 2 (de?96%), followed by trapping with various carbon, silicon, phosphorus and sulfur electrophiles. Cleavage of the monosubstituted hydrazones 3 led to monosubstituted ketones 4 (ee?98%). Further ortho-substitution of the hydrazones 3 afforded 2,2?-disubstituted hydrazones 5, which could be cleaved to disubstituted ferrocenyl diketones 6 (ee?99%). The new methodology allows a broad and flexible fine-tuning of ferrocenyl ligands desired in asymmetric catalysis. Ozonolysis or reductive hydrazone cleavage using TiCl3 or SnCl2 were the methods of choice to remove the auxiliary.

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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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Lithium tert-alkylperoxyacetylides were reacted with acetyl-, benzoyl, and 1,1?-dibenzoylferrocenes to obtain previously unknown ferrocene-containing acetylenic mono- and diperoxy alcohols. Thermal stability of the products was evaluated.

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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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Deuterium exchange of certain substituted ferrocenes (under very mild basic conditions) occurs in only the substituted cyclopentadienyl-ring in non-statistical pattern; a ?->? (eta5->eta1) rearrangement mechanism is proposed to account for the novel pattern of exchange.

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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