Category: 1273-86-5

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Ferrocene compounds XXIII. Synthesis and reactions of the new type of methyl ferrocyloxyalkanoates

The new types of ferrocenyloxaaliphatic acid ester, FcCHROCHR?COOMe (R = H, Me, Ph; R? = H, Me) (7) have been prepared by the action of alkoxides derived from methyl glycolate or methyl lactate on the corresponding ferrocenylcarbinyl acetates (2) or N,N,N-trimethylferrocylammonium iodides (4). The esters obtained were accompanied by a small quantity of oligomeric esters, FcCHR(OCHR?CO)nOMe (9), and with more or less ferrocyl methyl ethers (8). As opposed to the alkaline hydrolysis of the analogous methyl benzoxyacetate (6) into benzoxyacetic acid (5) the acidification of sodium alkanoates 10 obtained by saponification of esters 7 gave unexpectedly the corresponding ferrocenylcarbinols 1. In a similar way the esters 7 were converted into mixtures of the mentioned carbinols and diferrocyl ethers 11 under action of aqueous hydrochloric acid. The mechanisms of the reactions 10 ? 1 and 7 ? 1, 11 are discussed.

Ferrocene compounds XXIII. Synthesis and reactions of the new type of methyl ferrocyloxyalkanoates

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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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Ruthenium and osmium complexes containing 2-(aminomethyl)pyridine (Ampy)-based ligands in catalysis

This account focuses on the application in catalysis of ruthenium and osmium complexes containing 2-(aminomethyl)pyridine (Ampy)-based ligands. The combination of these aminoalkylpyridine ligands with appropriate phosphines affords ruthenium and osmium systems displaying unprecedented high catalytic activity and productivity in a variety of organic transformations such as hydrogenation by hydrogen transfer and dihydrogen, dehydrogenation, racemization, and alkylation.

Ruthenium and osmium complexes containing 2-(aminomethyl)pyridine (Ampy)-based ligands in 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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Synthesis and electrochemical properties of slipped-cofacial porphyrin dimers of ferrocene-functionalized Zn-imidazolyl-porphyrins as potential terminal electron donors in photosynthetic models

A systematic series of ferrocene-functionalized Zn-imidazolyl-porphyrins were synthesized to assemble into the slipped-cofacial porphyrin dimers through imidazolyl-to-zinc complementary coordination as artificial photosynthetic models. Direct substitution at the meso position of the porphyrin ring with ferrocence and octamethylferrocene leads to the characteristic electronic structures, while the ferrocene substituents through phenylene-ethenylene and phenylene-ethylene spacers mitigate the electronic communications. Bathochromic shift of Q band, fluorescence quenching, and redox potentials of porphyrin ring are rationalized by the degree of electron-donating ability of the terminal ferrocenes. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.

Synthesis and electrochemical properties of slipped-cofacial porphyrin dimers of ferrocene-functionalized Zn-imidazolyl-porphyrins as potential terminal electron donors in photosynthetic models

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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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Biodegradable Conducting Polymer Coating to Mitigate Early Stage Degradation of Magnesium in Simulated Biological Fluid: An Electrochemical Mechanistic Study

The application of a biodegradable conducting polymer coating based on a polythiophene composite (PTC) to mitigate degradation of magnesium in an in vitro environment is reported. The rationale behind the study is to advance a bioactive coating to control the rapid early stage degradation of the magnesium and prevent inflammatory reactions and physiological complications, while, in the long term, the coating degrades, followed by the full degradation of the magnesium implant. The conducting polymer in this study is deposited on a bioabsorbable medical grade magnesium alloy, AZNd, through layer-by-layer deposition, and the degradation behavior in simulated biological fluid is studied electrochemically. The possibility of a synergistic effect by combining praseodymium conversion coating together with the conducting polymer coating in protecting magnesium is also examined. Results show that the highest level of corrosion mitigation is afforded by the combination of praseodymium conversion and the conducting polymer coating layers. Electrochemical models are advanced to explain the electroactivity of the conducting polymer across the film as well as at the interface with electrolyte and substrate. Based on the physical and electrochemical evidence, the barrier effect is proposed as the main protection mechanism.

Biodegradable Conducting Polymer Coating to Mitigate Early Stage Degradation of Magnesium in Simulated Biological Fluid: An Electrochemical Mechanistic 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

 

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Sensitive detection of serum creatinine based on beta-cyclodextrin- ferrocenylmethanol modified screen-printed electrode

Ferrocenylmethanol (Fc-OH) is included in beta-cyclodextrin (beta-CD) to form the beta-CD-Fc-OH complex by host-guest supramolecular interaction. beta-CD dissociates from the beta-CD-Fc-OH complex due to the conversion of Fc-OH to Fc+-OH under a stimulus of oxidant. In our study, Fc-OH is oxidized after a series of enzymatic reactions of creatinine, which blocks the other means for oxidation of Fc-OH. And the background noise is reduced for testing for serum creatinine (sCr). The chronoamperometry signal for creatinine (with a constant potential -0.3 V vs. Ag/AgCl) increases linearly in the 1 – 1000 muM range, with a limit of detection as low as 0.5 muM. The amperometric potential of -0.3 V greatly prevents the interference of various redox substances in serum. The biosensor was used to test 120 clinical specimens and the results showed a linear correlation with the biochemical analyzer (R2 = 0.9885). The biosensor could be applied to clinical trials and offers good prospects for clinical sCr detection.

Sensitive detection of serum creatinine based on beta-cyclodextrin- ferrocenylmethanol modified screen-printed electrode

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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 novel side-chain ferrocene-containing polymer by combination of Cu(0)-mediated SET-LRP of acrylonitrile and post-modification

Well-defined side-chain ferrocene-containing polymers have been synthesized by post-modification of well-defined polyacrylonitrile (PAN). PAN prepared by Cu(0)-mediated single-electron transfer living radical polymerization was further modified using sodium azide and ammonium chloride (NH4Cl) to yield polymeric materials with vinyltetrazole units. Side-chain ferrocene-containing polymer was prepared by vinyltetrazole units and hydroxymethylferrocene after Mitsunobu reaction. FTIR, 1H NMR, UV?Vis spectroscopy and thermogravimetric analysis were used to identify the structure of the target product. After linked the ferrocene unit, the final polymer showed typical redox property?with?a?more negative?redox?potential (E1/2).

A novel side-chain ferrocene-containing polymer by combination of Cu(0)-mediated SET-LRP of acrylonitrile and post-modification

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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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Detection of proteins on membranes and in microchannels using copper staining combined with scanning electrochemical microscopy

Scanning electrochemical microscopy (SECM) and copper staining are combined to achieve visualisation of proteins on surfaces. Proteins are adsorbed on a polyvinylidene fluoride (PVDF) membrane or on a polyethylene terephthalate (PET) surface and stained using a standard protocol involving copper salts. Salts are then reduced to copper and detected by SECM with ferrocene methanol as a redox mediator in aqueous solution. During the SECM scan, the potential is held at a value at which the oxidation of the redox mediator occurs and a positive feedback current is detected when scanning over copper clusters. A negative feedback is observed elsewhere. This method enables unspecific protein adsorption mapping on polymeric membranes and into microchannels without any requirement of enzymatic activity or affinity to a labelled secondary reporter.

Detection of proteins on membranes and in microchannels using copper staining combined with scanning electrochemical microscopy

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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

 

Reference of 1273-86-5, 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, 1273-86-5, molcular formula is C11H3FeO, introducing its new discovery.

Synthesis, structure and enantiomeric resolution of ferrocenylalkyl mercaptoazoles. Antitumor activity in vivo

Ferrocenylalkyl 2-mercaptobenzimidazoles 3 (a-e) and 2-mercaptobenzo[d]thiazole-2(3H)-thiones 5 (a-e) were prepared via the reaction of the alpha-(hydroxy)alkyl ferrocenes, FcCHR(OH) (1a-e; Fc = ferrocenyl; R = H, Me, Et, i-Pr, Ph), either with thiobenzimidazole in acetone at room temperature in the presence of TFA (catalytic amounts), in yields of 55-74%, or with thiobenzothiazole in methylendicloride in presence of aqueous HBF4 (equimolar amounts) at r.t.; in yields of 41-58%. The structures, electrochemical properties and enantiomeric resolution 3a-e and 5a-e (using HPLC on modified amylose as chiral selector) were investigated. In cyclic voltammetry all studied compounds exhibited a reversible one-electron oxidation-reduction wave owing to the ferrocene-ferricenium redox couple with a positive shift (0.56-0.80 V) compared with that of ferrocene (0.50 V). X-ray determinations of molecular structures of 3-ferrocenylmethylbenzo[d]thiazole-2(3H)-thione (5a) 3-ferrocenylethylbenzo[d]thiazole-2(3H)-thione (5b) and 3-ferrocenylphenylmethylbenzo[d]thiazole-2(3H)-thione (5d) were carried out. The toxicity and antitumor activity of N-(ferrocenylethyl)-2-thiobenzimidazole (3b) were evaluated in vivo. Maximum tolerated dose (MTD) value for the compound 3b was found to be equal to 800 mg kg-1. The effectiveness of compound under investigation against murine solid tumor system, carcinoma Ca755 (Ca755), was studied in a wide range of doses and significant antitumor effects were found. The index of tumor growth inhibition (TGI) on Ca755 equaled 87% in comparison with control.

Synthesis, structure and enantiomeric resolution of ferrocenylalkyl mercaptoazoles. Antitumor activity in vivo

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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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Diamond Phase (sp3-C) Rich Boron-Doped Carbon Nanowalls (sp2-C): Physicochemical and Electrochemical Properties

The growth of B-CNW with different boron doping levels controlled by the [B]/[C] ratio in plasma, and the influence of boron on the obtained material’s structure, surface morphology, electrical properties, and electrochemical parameters, such as -DeltaE and k, were investigated. The fabricated boron-doped carbon nanowalls exhibit activity toward ferricyanide redox couple, reaching the peak separation value of only 85 mV. The flatband potential and the concentration of boron carriers were estimated in the B-CNW samples using the Mott-Schottky relationship. It was shown that the vertically oriented carbon planes are characterized by p-type conductivity and very high hole-acceptor concentration (3.33 ¡Á 1023 cm-3 for a highly doped sample), which provides high electrical conductivity. The enhanced electrochemical performance of B-CNWs electrodes is an advantageous feature that can be applied in ultrasensitive detection or energy storage devices. (Graph Presented).

Diamond Phase (sp3-C) Rich Boron-Doped Carbon Nanowalls (sp2-C): Physicochemical and Electrochemical Properties

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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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Simultaneous arrangement of up to three different molecules on the pore surface of a metal-macrocycle framework: Cooperation and competition

Porous crystals are excellent materials with potential spatial functions through molecular encapsulation within the pores. Co-encapsulation of multiple different molecules further expands their usability and designability. Herein we report the simultaneous arrangement of up to three different guest molecules, TTF (tetrathiafulvalene), ferrocene, and fluorene, on the pore surfaces of a porous crystalline metal-macrocycle framework (MMF). The position and orientation of adsorbed molecules arranged in the pore were determined by single-crystal X-ray diffraction analysis. The anchoring effect of hydrogen bonds between the hydroxy groups of the guest molecules and inter-guest cooperation and competition are significant factors in the adsorption behaviors of the guest molecules. This finding would serve as a design basis of multicomponent functionalized nanospaces for elaborate reactions that are realized in enzymes.

Simultaneous arrangement of up to three different molecules on the pore surface of a metal-macrocycle framework: Cooperation and competition

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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