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Substituent effects of 1,2-dithiole groups on the electrochemical oxidation of some ferrocenyl-1,2-dithiole compounds

New ferrocenyl compounds substituted by sulfur containing groups were synthesized leading to ferrocenyl-3H-1,2-dithiole-3-thiones and related compounds. The substituent of the ferrocene was a [3-thioxo-3H-1,2-dithiol]-4 or 5-yl, a [3-oxo-3H-1,2-dithiol]-4 or 5- yl or a [3-methylsulfanyl-3H-1,2-dithiolium]-4 or 5-yl cation group. Their anodic behavior was studied by cyclic voltammetry at a Pt electrode in aprotic solvent. All synthesized ferrocenes exhibited a one-electron reversible oxidation leading to the corresponding ferricinium cation. At low potential scan, the irreversible oxidation of 5-ferrocenyl-3H-1,2-dithiole-3-thione was observed and attributed to a dimerization involving the dithiolethione group. Redox potential of the reversible oxidation allowed the determination of the electronic effect of the 1,2-dithiole groups. The Hammett sigmap constants of the dithiole substituents were obtained from linear correlation between oxidation potentials and electronic effects. The results showed that the [3-thioxo-3H-1,2-dithiol]-5-yl and the [3-methylsulfanyl-3H-1,2-dithiolium]-5-yl cation groups were strong inductive electron withdrawing substituents characterized by sigmap values of 0.55 and 0.97, respectively.

Substituent effects of 1,2-dithiole groups on the electrochemical oxidation of some ferrocenyl-1,2-dithiole compounds

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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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Application of Biginelli reaction to the synthesis of ferrocenylpyrimidones and [3]-ferrocenophane-containing pyrimido[4,5-d]pyrimidinediones

A series of ferrocene-containing mono- and bis-dihydropyrimidines (DHP’s) were prepared by boric acid mediated three-component Biginelli reactions of formyl- and 1,1?-diformylferrocene, 1,3-dioxo-components and urea. A few further transformations including hydrogenolysis of a benzyl 4-ferrocenyl-DHP-5-carboxylate were also performed. Novel cis-fused saturated pyrimido[4,5-d]pyrimidine-2,7(1H,3H)-diones incorporating [3]-ferrocenophane moiety were constructed by means of iron(III)-catalyzed Biginelli-like condensations of 1,1?-diformylferrocene with urea and in situ generated methyl ketone-derived silyl enol ethers. The structures of the new compounds were established by IR and NMR spectroscopy, including HMQC, HMBC and DEPT measurements.

Application of Biginelli reaction to the synthesis of ferrocenylpyrimidones and [3]-ferrocenophane-containing pyrimido[4,5-d]pyrimidinediones

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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

 

One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, SDS of cas: 1273-94-5, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 1273-94-5, Name is 1,1′-Diacetylferrocene, molecular formula is C14H6FeO2

A ferrocene base class redox reversible of surface active agent and its preparation method (by machine translation)

A ferrocene base class redox reversible of surface active agent and its preparation method, relates to oxidation-reduction switch type surface active agent field. Previous precursor compound ferrocene, acetyl chloride, zinc amalgam, bromo eleven acid, thionyl chloride and dimethylamine as raw material preparation, to obtain a ferrocene base class redox reversible surface active agent, the invention synthetic surfactant molecule is easy to prepare, effectively improves the intermediate II b of acyl ferrocene yield, and puts forward a new feeding sequence, thereby effectively preventing the oxidation reaction leading to the ferrocene to reduce this problem. The surface active agent can be used as the electrode surface modification material is used for the detection of glucose. (by machine translation)

A ferrocene base class redox reversible of surface active agent and its preparation method (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

 

Chemistry is traditionally divided into organic and inorganic chemistry. Quality Control of 1,1′-Diacetylferrocene, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent£¬Which mentioned a new discovery about 1273-94-5

A ferrocene naphthyridine derivatives and its preparation and use (by machine translation)

The invention relates to a kind of ferrocene naphthyridine derivatives and its preparation and use. The design of the invention the synthetic model ferrocene naphthyridine derivatives of high productivity, cost, can effectively identify and absorb the Hg in the liquid2 + , And Cu2 + There are also identification function, in purifying the environment have a wide range of application prospect. (by machine translation)

A ferrocene naphthyridine derivatives and its preparation and use (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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Synthesis of biologically active Co(II), Cu(II), Ni(II), and Zn(II) complexes of symmetrically 1,1?-disubstituted ferrocene-derived compounds

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.

Synthesis of biologically active Co(II), Cu(II), Ni(II), and Zn(II) complexes of symmetrically 1,1?-disubstituted ferrocene-derived compounds

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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

 

In heterogeneous catalysis, the catalyst is in a different phase from the reactants. Computed Properties of C14H6FeO2, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 1273-94-5, name is 1,1′-Diacetylferrocene. In an article£¬Which mentioned a new discovery about 1273-94-5

Synthesis of 1,1?-diacetylferrocene dioxime esters

1,1?-Diacetylferrocene dioxime was synthesized by the reaction of 1,1?-diacetylferrocene with hydroxylamine. The dioxime reacts readily with carboxylic acids chlorides in the presence of pyridine with the formation of 1,1?-diacetylferrocene dioxime esters.

Synthesis of 1,1?-diacetylferrocene dioxime esters

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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

 

Application of 1273-94-5, Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics.In a document type is Article, and a compound is mentioned, 1273-94-5, 1,1′-Diacetylferrocene, introducing its new discovery.

Stereo- and enantioselectivity in catalytic hydrogenolysis of chiral substituted ferrocenes to give cyclopentanes

The catalytic hydrogenolysis of 1,2-disubstituted ferrocenes having planar chirality and functional groups such as carboxyl (including ester) or tertiary amino proceeds under mild conditions (1 atm of H2, Pd/C, CF3COOH, 50 deg C) with the retention of functional groups in the cyclopentane products.Stereosectivity has been observed for the examples investigated, the diastereomeric ratio, trans: cis being close to 4:1, but optically inactive products are formed the enantiomeric ferrocenes.In contrast, hydrogenolysis of enantiomeric alpha-(N,N-dimethylamino)ethylferrocene gives an optically active alpha-(N,N-dimethylamino)ethylcyclopentane with retention of configuration at the alpha-carbon, whose bonds are not affected during the hydrogenolysis.

Stereo- and enantioselectivity in catalytic hydrogenolysis of chiral substituted ferrocenes to give cyclopentanes

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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

 

Chemistry is traditionally divided into organic and inorganic chemistry. Product Details of 1273-94-5, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent£¬Which mentioned a new discovery about 1273-94-5

Redox routes to arenechromium complexes of two-, three- and four-electron alkynes: Structure and bonding in paramagnetic [Cr(CO)L(eta-RC?CR)(eta-arene)]+

X-Ray structural studies on the redox pair [Cr(CO)2(eta-PhC?CPh)(eta-C6Me5H)] z (z = 0 and 1) show that one-electron oxidation of the neutral complex results in a shortening of the Cr-Calkyne bonds and a lengthening of the Cr-C(O) bonds, consistent with depopulation of a HOMO antibonding with respect to the metal-alkyne interaction. Oxidation leads to an increase in the substitutional lability of the Cr-CO bonds so that [Cr(CO)2-(eta-RC?CR)(eta-C6Me6)] + (R = Ph or C6H4OMe-p) reacts with Lewis bases to give [Cr(CO)L(eta-RC?CR)(eta-C6Me6)]+ {L = CNXyl, P(OMe)3 and P(OCH2)3CEt}, X-ray studies on which show a rotation of the alkyne to align with the remaining Cr-CO bond. ESR spectroscopic studies on [Cr(CO)L(eta-RC?CR)(eta-C6Me6)]+ show delocalisation of the unpaired electron onto the alkyne ligand, consistent with its description as a three-electron donor. The cations [Cr(CO)L(eta-RC?CR)(eta-C6Me6)]+ undergo both one-electron reduction and oxidation, and chemical oxidation of [Cr(CO){P(OCH2)3CEt} (eta-p-MeOC6H4C?CC6H4OMe-p)( eta-C6Me6)]+ with AgPF6 gives the dication [Cr(CO){P(OCH2)3CEt}(eta-p-MeOC6H4 C?CC6H4OMe-p)(eta-C6Me6)] 2+. Thus the two-electron alkyne of [Cr(CO)2-(eta-RC?CR)(eta-C6Me6)] is converted into the four-electron alkyne of [Cr(CO)L(eta-RC?CR)(eta-C6Me6)]2+ by an ECE (E = electrochemical, C = chemical) process in which all of the intermediates have been fully characterised.

Redox routes to arenechromium complexes of two-, three- and four-electron alkynes: Structure and bonding in paramagnetic [Cr(CO)L(eta-RC?CR)(eta-arene)]+

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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

 

In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 1273-94-5, name is 1,1′-Diacetylferrocene, introducing its new discovery. Safety of 1,1′-Diacetylferrocene

Synthetic Model Complex of the Key Intermediate in Cytochrome P450 Nitric Oxide Reductase

Fungal denitrification plays a crucial role in the nitrogen cycle and contributes to the total N2O emission from agricultural soils. Here, cytochrome P450 NO reductase (P450nor) reduces two NO to N2O using a single heme site. Despite much research, the exact nature of the critical “Intermediate I” responsible for the key N-N coupling step in P450nor is unknown. This species likely corresponds to a Fe-NHOH-type intermediate with an unknown electronic structure. Here we report a new strategy to generate a model system for this intermediate, starting from the iron(III) methylhydroxylamide complex [Fe(3,5-Me-BAFP)(NHOMe)] (1), which was fully characterized by 1H NMR, UV-vis, electron paramagnetic resonance, and vibrational spectroscopy (rRaman and NRVS). Our data show that 1 is a high-spin ferric complex with an N-bound hydroxylamide ligand that is strongly coordinated (Fe-N distance, 1.918 A Fe-NHOMe stretch, 558 cm-1). Simple one-electron oxidation of 1 at -80 C then cleanly generates the first model system for Intermediate I, [Fe(3,5-Me-BAFP)(NHOMe)]+ (1+). UV-vis, resonance Raman, and Moessbauer spectroscopies, in comparison to the chloro analogue [Fe(3,5-Me-BAFP)(Cl)]+, demonstrate that 1+ is best described as an FeIII-(NHOMe)? complex with a bound NHOMe radical. Further reactivity studies show that 1+ is highly reactive toward NO, a reaction that likely proceeds via N-N bond formation, following a radical-radical-type coupling mechanism. Our results therefore provide experimental evidence, for the first time, that an FeIII-(NHOMe)? electronic structure is indeed a reasonable electronic description for Intermediate I and that this electronic structure is advantageous for P450nor catalysis because it can greatly facilitate N-N bond formation and, ultimately, N2O generation.

Synthetic Model Complex of the Key Intermediate in Cytochrome P450 Nitric Oxide Reductase

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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

 

Chemistry is traditionally divided into organic and inorganic chemistry. name: 1,1′-Diacetylferrocene, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent£¬Which mentioned a new discovery about 1273-94-5

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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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