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1273-94-5, Name is 1,1′-Diacetylferrocene, belongs to iron-catalyst compound, is a common compound. COA of Formula: C14H6FeO2In an article, once mentioned the new application about 1273-94-5.

Synthesis, characterization and antitumor activities of 1,1′-diacetylferrocene dihydrazone containing a salicylaldehyde moiety and its complexes with pd(II) and pt(II)

A ferrocenyl ligand was prepared from condensation of 1,1′- diacetylferrocene dihydrazone with salicylaldehyde. Ligand forms 1:1 complexes with Pd(II) and Pt(II) in good yield. Characterization of the ligand and complexes was carried out using elemental analysis, infrared, 1H nuclear magnetic resonance and electronic absorption spectra. Anticancer activity of the prepared ligand and its complexes against human breast cancer cell line MCF-7 was determined, and the results were compared with the activity of the commonly used anticancer drug cisplatin. The results suggested that the prepared compounds possess significant antitumor activity comparable to the activity of cisplatin and may be potent anticancer agents for inclusion in modern clinical trials.

Synthesis, characterization and antitumor activities of 1,1′-diacetylferrocene dihydrazone containing a salicylaldehyde moiety and its complexes with pd(II) and pt(II)

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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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beta-Keto phosphines derived from ferrocene. Syntheses and structures of (L1) and trans-

The keto-phosphines (L1), <(Ph2PCH2C(O)(eta5-C5H4))2Fe> (L2) and <(Ph2PCH2C(O)(eta5-C5H4)C(O)CH3)> (L3) were respectively prepared by the reaction of Ph2PCl with the lithium enolates derived from acetylferrocene for L1, and 1,1′-bis(acetyl)ferrocene for L2 and L3.Ligand L1 crystallizes in the space group P1 with a 8.526(2), b 10.915(3), c 12.822(3) Angstroem, alpha 63.75(2), beta 69.04(2), gamma 70.77(2) deg, V 978.4 Angstroem3 and Z 2.The structure was solved and refined to R=0.034 and RW=0.042.The C5-rings are eclipsed (3.2 deg) and the plane of the keto group forms a dihedral angle of 13.1 deg with the C5H4 plane.In the complexes cis- and trans- (cis-1 and trans-1), <(o-C6H4CH2NMe2)PdClL1> (2), cis- (3), and (4) the phosphine ligand(s) behave as P-monodentate(s).The structure of trans-1 has been determined by X-ray diffraction at -145 deg C.The complex crystallizes in the monoclinic space group P21/c with a 10.622(7), b 12.647(7), c 15.59(1) Angstroem, beta 103.20(6) deg, V 2039 Angstroem3 and Z=2.The structure was solved and refined to R=0.037 and RW=0.053.The palladium atom lies on a centre of symmetry and the Pd-P and Pd-Cl bond lengths are respectively 2.314(1) and 2.287(1) Angstroem.The C5-rings of each ligand are slightly staggered (10.5 deg) and, as for L1, each keto group is almost parallel to the C5H4 plane (dihedral angle 8.9 deg).For the complex BF4, NMR and IR solution spectroscopy has shown that there is a dynamic exchange between chelating and P-monodentate L1.The possibility of using L2 as a binucleating ligand was demonstrated by the preparation of the trinuclear complex <((C10H8N)PdCl)2(mu-L2-P,P')> (6).The enolato complexes cis- (M=Pd (7), M=Pt (8)), and <(o-C6H4CH2NMe2)Pd(Ph2PCH=C(O)(eta5-C5H4)Fe(eta5-C5H5))> (9) were prepared in high yield by the reaction of NaH with complexes 1, 3, and 2, respectively.Complex 9 reacts with dimethylacetylenedicarboxylate to yield the alkenyl complex <(o-C6H4CH2NMe2)Pd(Ph2PCH(MeO2CC=CCO2Me))> (10), resulting from carbon-carbon coupling between the P bound enolate-carbon atom and the alkyne.All the complexes were characterized by elemental analysis, and 1H and 31P(1H) NMR and IR spectroscopy.

beta-Keto phosphines derived from ferrocene. Syntheses and structures of (L1) and trans-

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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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Study of ferrocenyl-substituted Co2(CO)6-bispropargylic alcohol complexes as substrates for the formation of chains and macrocycles

Treatment of [Fc-1-R1-1?-R2] (R1 = H, R2 = CH(O); R1 = H, R2 = CMe(O); R1 = R2 = CMe(O)) with LiC{triple bond, long}CCH2OLi (prepared in situ from HC{triple bond, long}CCH2OH and n-BuLi) affords the ferrocenyl-substituted but-2-yne-1,4-diol compounds of general formula [Fc-1-R1-1?-{CR(OH)C{triple bond, long}CCH2OH}] (R1 = R = H (1a); R1 = H, R = Me (1b); R1 = CMe(O), R = Me (1c)) in low to high yields, respectively (where Fc = Fe(eta5-C5H4)2). In the case of the reactions of [Fc-1-R1-1?-R2] (R1 = H, R2 = CH(O); R1 = R2 = CMe(O)), the by-products [Fc-1-R1-1?-{CR(OH)(CH2)3CH3}] (R1 = R = H (2a); R1 = CMe(O), R = Me (2c)) along with minor quantities of [Fc-1,1?-{CMe(OH)(CH2)3CH3}2] (3) are also isolated; a hydrazide derivative of dehydrated 2c, [1-(CMe{double bond, long}CHCH2CH2CH3)-1?-(CMe{double bond, long}NNH-2,4-(NO2)2C6H3)] (2c?), has been crystallographically characterised. Interaction of 1 with Co2(CO)8 smoothly generates the alkyne-bridged complexes [Fc-1-R1-1?-{Co2(CO)6-mu-eta2-CR(OH)C{triple bond, long}CCH2OH}] (R1 = R = H (4a); R1 = H, R = Me(4b); R1 = CMe(O), R = Me (4c)) in good yield. Reaction of 4a with PhSH, in the presence of catalytic quantities of HBF4 ¡¤ OEt2, gives the mono- [Fc-1-H-1?-{Co2(CO)6-mu-eta2-CH(SPh)C{triple bond, long}CCH2OH}] (5) and bis-substituted [Fc-1-H-1?-{Co2(CO)6-mu-eta2-CH(SPh)C{triple bond, long}CCH2SPh}] (6) straight chain species, while with HS(CH2)nSH (n = 2,3) the eight- and nine-membered dithiomacrocylic complexes [Fc-1-H-1?-{cyclo-Co2(CO)6-mu-eta2-CH(S(CH2)n-)C{triple bond, long}CCH2S-}] [n = 2 (7a), n = 3 (7b)] are afforded. By contrast, during attempted macrocyclic formation using 4b and HSCH2CH2OCH2CH2SH dehydration occurs to give [Fc-1-H-1?-{Co2(CO)6-mu-eta2-C({double bond, long}CH2)C{triple bond, long}CCH2OH}] (8). Single crystal X-ray diffraction studies have been reported on 2c?, 4b, 4c, 7b and 8.

Study of ferrocenyl-substituted Co2(CO)6-bispropargylic alcohol complexes as substrates for the formation of chains and macrocycles

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

 

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Synthesis and electrochemical properties of 1,1?-bis (benzo-1,3-dithiol-2-ylidene)ferrocene derivatives as novel electron donor compounds

A number of 1,1?-bis(benzo-1,3-dithiol-2-ylidene)ferrocene derivatives 7a-b and 12-14 based on the strong electron donating ability of 1,3-dithiole and ferrocene moieties were synthesized as new pi-donors. The structure and physical properties of these compounds were characterized both by experimental techniques and spectral analysis. These new classes of donor compounds were obtained in very high yields based on modification of the Wittig-Horner reaction and the 1,3-dithiole rings were separated by conjugated spacers including aryl-ferrocenyl- aryl. The electrochemical properties of the new compounds have been studied in comparison to DB-TTF 4 analogues, and the parent ferrocene donor by cyclic voltammetry (CV), using Pt electrode as the working electrode in CH2Cl2 solutions at room temperature. Three subsequent oxidation processes are observed as three oxidation waves associated only with two reduction processes. Polycrystalline samples of 14a-b are conducting sigma rt 14a=0.2 S cm-1 and sigma rt 14b=4.8¡Á10-4 S cm-1) respectively, while compounds 15 and 16 were found essentially as insulator (sigma rt<10-10 S cm-1). Synthesis and electrochemical properties of 1,1?-bis (benzo-1,3-dithiol-2-ylidene)ferrocene derivatives as novel electron donor compounds Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Quality Control of 1,1′-Diacetylferrocene, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 1273-94-5, in my other articles.

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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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Reference of 1273-94-5, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 1273-94-5, molcular formula is C14H6FeO2, introducing its new discovery.

Preparation of Optically Active alpha-Amino[3]ferrocenophanes – Building Blocks for Chelate Ligands in Asymmetric Catalysis

Treatment of 1,1?-diacetylferrocene (4) with dimethylamine and TiCl4 yielded the unsaturated dimethylamino-substituted [3]ferrocenophane product 5. Its catalytic hydrogenation gave the corresponding saturated [3]ferrocenophane system 6 (trans/cis ? 7:1). The rac-[3]ferrocenophane amine 6 was partially resolved (to ca. 80% ee) by means of L- or D-O,O?-dibenzoyltartrate salt formation. Treatment of 4 with the pure (R)- or (S)-methyl(1-phenylethyl)amine (8)/TiCl4 gave the corresponding optically active unsaturated [3]ferrocenophane amines (R)-(+)-9 and (S)-(-)-9, respectively. Their catalytic hydrogenation again proceeded trans-selectively, giving the corresponding saturated diastereomeric [3]ferrocenophane amines (1R,3R,5R)-10a and (1S,3S,5R)-10b [starting from (R)-9], their enantiomers ent-10a and ent-10b were obtained from (S)-9, but with a poor asymmetric induction (10a/10b < 2:1). Quaternization of 6 (CH3I) followed by amine exchange using (R)- or (S)-methyl(1-phenylethyl)amine (8), respectively, proceeded with overall retention. Subsequent chromatographic separation gave the pure diastereoisomers (1R,3R,5R)-10a and (1S,3S,5R)-10b [from (R)-8, ent-10a and ent-10b from (S)-8] in > 60% yield. Subsequently, the benzylic (1-phenylethyl) auxiliary was removed from the nitrogen atom by catalytic hydrogenolysis to yield the enantiomerically pure (> 98%) ([3]ferrocenophanyl)methylamines (1R,3R)-11 and (1S,3S)-11, respectively, which were converted into the corresponding dimethylamino-substituted [3]ferrocenophanes (1R,3R)-6 and (1S,3S)-6. Each enantiomer from the following enantiomeric pairs was isolated in its pure form and characterized by X-ray diffraction: (R)-9/(S)-9; (1R,3R,5R)-10a/(1S,3S,5S)-10a; (1R,3R,5S)-10b/(1S,3S,5R)-10b; (1R,3R)-11/(1S,3S)-11. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Preparation of Optically Active alpha-Amino[3]ferrocenophanes – Building Blocks for Chelate Ligands in Asymmetric Catalysis

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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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Structure and bonding in the d4/d3 alkyne redox pairs [WX(CO)(MEC?CMe)Tp’](z) (X = F, Cl, Br and I; z = 0 and 1): Halide stabilisation of electron deficient metal alkyne complexes

X-Ray structural and EPR spectroscopic studies of the redox-related pairs [WX(CO)(MeC=CMe)Tp’](z) (X = F, Cl, Br and I; z = 0 and 1) [Tp’ = hydrotris(3,5-dimethylpyrazolyl)borate] are consistent with the HOMO of the d4 (z = 0) species being pi-bonding with respect to the W-CO bond, pi- antibonding with respect to the W-X bond, and delta-bonding with respect to the W-alkyne bond.

Structure and bonding in the d4/d3 alkyne redox pairs [WX(CO)(MEC?CMe)Tp’](z) (X = F, Cl, Br and I; z = 0 and 1): Halide stabilisation of electron deficient metal alkyne complexes

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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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Synthesis, characterization and coordination properties of Cu(II), Co(II), Ni(II) and Zn(II) complexes with a novel asymmetric 1,1?-ferrocene-derived Schiff base ligand

A novel asymmetric 1,1?-ferrocene-derived Schiff base ligand has been prepared by the condensation reaction of 1,1?-diacetylferrocene with 2-aminopyridine and 2-aminothiazole. Its transition metal complexes of the type [M(L)]Cl2 and [M(L)(Cl2)] [M = Cu(II),Co(II) and Ni(II)] have been prepared and characterized by their physical, analytical and spectral data. The Cu(II) complex shows square-planar whereas the Co(II), Ni(II) and Zn(II) complexes show octahedral geometry.

Synthesis, characterization and coordination properties of Cu(II), Co(II), Ni(II) and Zn(II) complexes with a novel asymmetric 1,1?-ferrocene-derived Schiff base ligand

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Syntheses and structural characterization of ferrocene-containing double-helicate and mononuclear copper(II) and silver(I) complexes

The self-assembly and structural characterization of the new ferrocene-containing dicopper(II) double helicate [Cu2L12] (1) and related copper(II) complex [CuL2(CH3CN)] [ClO4]2 (2) and silver(I) complexes [AgL2(CH3CN)][BF4] (3) and [AgL2] [BF4](4) have been achieved. These complexes are derived from inexpensive and easy-to-prepare ferrocene-containing bisbidentate Schiff-base ligands H2L1, [(C6H4)(OH)CHNNC(CH3) (C5H4)]2Fe, and L2, [(C5H4N)CHNNC(CH3) (C5H4)]2Fe. The neutral double-helical dicopper(II) complex 1 crystallizes in a polar space group. The two ferrocene-containing ligands strand interwined about each other and around the two tetrahedral copper ions in a double-helical fashion, with the Cu&mellip;Cu separation being 9.45 A . The four metal centers are coplanar and form a slightly distorted rhombus with sides of ca. 5.8 A . Reaction of the ligand L2 and copper(II) constructed a mononuclear copper complex, 2. X-ray structural analysis reveals that the copper(II) atom is coordinated in a distorted square pyramidal geometry, with four nitrogen atoms from the two bidentate bind sites forming the basal plane; the acetonitrile nitrogen atom occupies the apical position. The molecular structure of the silver(I) complex 3 is quite similar to that of copper complex 2, with the silver(I) surprisingly coordinated in a square pyramidal geometry. The silver(I) atom in mononuclear silver complex 4 is coordinated in a new square planar fashion. The result presented here shows that while the ligand (L1)2- can bridge two metal ions to give a double helicate with Cu(II), the ligand L2 acts as a tetradentate ligand chelate to a single metal center in its structurally characterized complexes with Cu(II) and Ag(I). Crystal structures of the free ligand H2L1 and L2 are also reported for comparison.

Syntheses and structural characterization of ferrocene-containing double-helicate and mononuclear copper(II) and silver(I) complexes

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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 flexible approach to strained sandwich compounds: Chiral [1]ferrocenophanes with boron, gallium, silicon, and tin in bridging positions

The enantiomerically pure dibromoferrocene 3 [(Sp,S p)-1,1?-dibromo-2,2?-di(isopropyl)ferrocene], equipped with two iPr groups in alpha positions, was prepared using known “Ugi amine” chemistry. Species 3 was targeted in order to gain access to new [1]ferrocenophanes ([1]FCPs) to be used as monomers for ring-opening polymerization. The iPr groups on the sandwich unit were introduced to stabilize bridging moieties, as well as to increase solubilities of targeted metallopolymers. The planar chiral dibromide 3 can quantitatively be lithiated at 0 C [2 equiv nBuLi, hexanes/thf (9:1), 30 min]. Salt-metathesis reactions with respective element dichloride species gave chiral [1]FCPs with a variety of bridging moieties [ERx=Ga[2-(Me2NCH 2)C6H4] (4 a), SiMe2 (4 b), SntBu2 (4 c), BNiPr2 (4 d)]. The new [1]FCPs were fully characterized including single-crystal X-ray analysis. The stabilizing iPr groups on the Cp rings increase the thermal stabilities of 4 b-d compared to known [1]FCPs, equipped with the same bridging moieties. All three compounds 4 b-d are volatile and could be isolated by vacuum sublimation. Our new approach to [1]FCPs has the potential to overcome many of the existing difficulties in ferrocenophane chemistry, such as limited stability of starting monomers and low solubilities of resulting polyferrocenes. Closing the gap: The preparation of [1]ferrocenophanes with a variety of bridging elements was accomplished by using chiral ferrocene derivatives (see scheme). The isopropyl groups on the sandwich unit serve as protective and solubilizing moieties. The new synthetic approach is superior to the common synthesis of [1]ferrocenophanes, when dilithioferrocene-tmeda is used as the starting material. Copyright

A flexible approach to strained sandwich compounds: Chiral [1]ferrocenophanes with boron, gallium, silicon, and tin in bridging positions

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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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Synthesis of Diferrocenyl Hydrazone?Enone Receptor Molecules ? Electronic Communication, Metal Binding, and DFT Study

Four new diferrocenyl hydrazone?enone compounds were obtained through a two-step reaction process involving 1,1?-diacetylferrocene, hydrazides, and ferrocenecarboxaldehyde. The structural characterization of two compounds, 6 and 7, through single-crystal X-ray diffraction showed the presence of a stable eclipsed conformation with the two ferrocenyl moieties oriented in trans geometries. The electrochemical and metal-ion sensing properties of the diferrocenyl-bifunctionalized compounds were explored to understand their potential in electronic communication and as receptor molecules. Compounds 1,1?-[(eta5-C5H5)Fe(eta5-C5H4)CH=CHC(O)(eta5-C5H4)Fe{(eta5-C5H4)C(CH3)=N?N(H)C(O)?R}] [R = C6H4OH (6), C6H4N-p (7)], showed selective interactions with Pb2+cations and distinct binding interactions with bovine serum albumin (BSA) protein. The mode of the metal?receptor interaction was established through DFT studies. The redox properties of the diferrocenyl compounds with variable end groups revealed distinct electronic communication between the two electroactive groups.

Synthesis of Diferrocenyl Hydrazone?Enone Receptor Molecules ? Electronic Communication, Metal Binding, and DFT Study

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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