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Transalkylation and Migration of N-Substituent upon Alkylation of 1,2,3-Triazoles Containing Good Leaving N-Substituents

The synthesis of four new 1,2,3-triazole derivatives and seven 1,2,3-triazolium salts that contain an organometallic group (i.e., cymantrenyl and ferrocenyl) at either the N-1, N-2, or N-3 position was realized. The alkylation of organometallic and organic triazole derivatives was investigated, and as a result of these studies, it was found that the presence of a good leaving group at the heterocyclic nitrogen atom led to transalkylation and subsequent migration of the N-1 substituent to the N-2 position of the triazole moiety. The nucleophilicity of the counterion of the triazolium salt influenced the transalkylation and isomerization processes, which suggests that the elimination of the N-substituent most likely occurs though a concerted mechanism with nucleophilic assistance from the counterion. Thus, a new approach to the synthesis of 2,4-disubstituted 1,2,3-triazoles has been developed.

Transalkylation and Migration of N-Substituent upon Alkylation of 1,2,3-Triazoles Containing Good Leaving N-Substituents

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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

 

Extended knowledge of Ferrocenemethanol

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Simple route to ferrcenyl(alkyl)imidazoles

A suitable method for the synthesis of ferrocenyl(alkyl)imidazoles is proposed. The treatment of alpha-ferrocenylcarbinols with N,N?-carbonyldiimidazole affords the title compounds, are in more than 80% yields.

Simple route to ferrcenyl(alkyl)imidazoles

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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

 

Discovery of Ferrocenemethanol

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Regularities in formation of intramolecular hydrogen bonds with the metal atom Part I. alpha-Metallocenylcarbinols of the iron subgroup

Conditions for the formation of intramolecular hydrogen bonds in alpha-metallocenylcarbinols of the iron subgroup (M = Fe, Ru, Os) are determined.The combination of IR spectral data with conformational calculations has revealed situations where hydrogen bonding with the metal atom is determined by conformational preference.General rules govering the influence of the nature of the metal atom and the effect of substituents in the carbinol group and the cyclopentadienyl rings on the formation constants and relative stability of OH…Me intramolecular hydrogen bonds, on the proton-donating ability of the OH group and on the competition between intra- and intermolecular hydrogen bonds during self-association in the crystal, are estabished.

Regularities in formation of intramolecular hydrogen bonds with the metal atom Part I. alpha-Metallocenylcarbinols of the iron subgroup

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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

 

Archives for Chemistry Experiments of 1273-86-5

I hope this article can help some friends in scientific research. I am very proud of our efforts over the past few months and hope to 1273-86-5, help many people in the next few years.Quality Control of Ferrocenemethanol

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A voltammetric investigation of the reactions between surface-confined amines and quinones on gold electrodes: Evidence for imine formation

A surface-confined layer containing naphthoquinone was prepared by reacting 2,3-dichloronaphthoquinone with the amino tail groups of an aminoethanethiolate-modified vapor-deposited gold surface; this surface layer was then reacted with beta-ferrocenylethylamine. These modified gold electrodes were examined with cyclic staircase voltammetry in aqueous HClO4 at the completion of each step in this sequence of reactions. The voltammetric signature for the 2e-, 2H+ reduction of the quinoid redox centers disappeared after the ferrocene compound was reacted with the naphthoquinone surface layer; furthermore, the surface coverage of ferrocene was twice that expected on the basis of a 1:1 reaction between the surface-bound naphthoquinone and beta-ferrocenylethylamine. These results suggest that the latter reacts with the naphthoquinone carbonyl groups to form a surface-confined di-imine, which cannot be reduced within the electrochemical potential window of aqueous HClO4. In similar experiments, 2-[4?-(beta-ferrocenylethylaminocarbonyl)phenyl]-1,4-naphthoquinone and 2-[2?-(beta-ferrocenylethylaminocarbonyl)-ethyl]anthraquinone were synthesized and reacted with aminoethanethiolate-modified gold surfaces. When examined at a platinum electrode in nonaqueous solvents, both of the freely diffusing compounds exhibited two pairs of voltammetric waves characteristic of quinoid and ferrocene functionalities. However, only the ferrocene redox centers of the resulting surface-confined layers were electroactive, suggesting that the reaction of these compounds with the surface-confined aminoethanethiolate involves conversion of the quinoid carbonyls to imines.

A voltammetric investigation of the reactions between surface-confined amines and quinones on gold electrodes: Evidence for imine formation

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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

 

Final Thoughts on Chemistry for 1273-86-5

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Integrated multienzyme electrochemical biosensors for monitoring malolactic fermentation in wines

Integrated amperometric biosensors for the determination of l-malic and l-lactic acids were developed by coimmobilization of the enzymes l-malate dehydrogenase (MDH) and diaphorase (DP), or l-lactate oxidase (LOX) and horseradish peroxidase (HRP), respectively, together with the redox mediator tetrathiafulvalene (TTF), on a 3-mercaptopropionic acid (MPA) self-assembled monolayer (SAM)-modified gold electrode by using a dialysis membrane. The electrochemical oxidation of TTF at +100 mV (vs. Ag/AgCl), and the reduction of TTF+ at -50 mV were used for the monitoring of the enzyme reactions involved in l-malic and l-lactic acid determinations, respectively. Experimental variables concerning the biosensors composition and the detection conditions were optimized for each biosensor. Good relative standard deviation values were obtained in both cases for the measurements carried out with the same biosensor, with no need of cleaning or pretreatment of the bioelectrodes surface, and with different biosensors constructed in the same manner. After 7 days of continuous use, the MDH/DP biosensor still exhibited 90% of the original sensitivity, while the LOX/HRP biosensor yielded a 91% of the original response after 5 days. Calibration graphs for l-malic and l-lactic were obtained with linear ranges of 5.2 ¡Á 10-7 to 2.0 ¡Á 10-5 and 4.2 ¡Á 10-7 to 2.0 ¡Á 10-5 M, respectively. The calculated detection limits were 5.2 ¡Á 10-7 and 4.2 ¡Á 10-7 M, respectively. The biosensors exhibited a high selectivity with no significant interferences. They were applied to monitor malolactic fermentation (MLF) induced by inoculation of Lactobacillus plantarum CECT 748T into a synthetic wine. Samples collected during MLF were assayed for l-malic and l-lactic acids, and the results obtained with the biosensors exhibited a very good correlation when plotted against those obtained by using commercial enzymatic kits.

Integrated multienzyme electrochemical biosensors for monitoring malolactic fermentation in wines

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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

 

The Absolute Best Science Experiment for 1,1′-Diacetylferrocene

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One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, Product Details of 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

Preparation of ferrocenyl mono- and dienone derivatives through aldol condensation of 1,1?-diacetylferrocene with aromatic aldehydes in dry conditions

1,1?-Diacetylferrocene was condensed with aromatic aldehydes without solvent in the presence of solid NaOH. Diacetylferrocene can give good yields of mono- or diene with either one or two molecules of a wide range of aldehydes depending only on the stoichiometry. Cyclization to ferrocenphane does not occur in this condition.

Preparation of ferrocenyl mono- and dienone derivatives through aldol condensation of 1,1?-diacetylferrocene with aromatic aldehydes in dry conditions

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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

 

More research is needed about Vinylferrocene

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One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, Formula: C12H3Fe, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 1271-51-8, Name is Vinylferrocene, molecular formula is C12H3Fe

Internal adduct formation of active intramolecular C4-bridged frustrated phosphane/borane Lewis pairs

The tetramethylene-bridged PMes2/B(C6F 5)2 frustrated Lewis pair (FLP) 8 was prepared by hydroboration of Mes2P-(CH2)2CH=CH2 with HB(C6F5)2. It is an active FLP that splits dihydrogen under mild conditions and, consequently, serves as a metal-free hydrogenation catalyst for a variety of substrates. It also reacts typically with terminal acetylenes. The C4-bridged FLP 23 was prepared by HB(C6F5)2 hydroboration of 1- dimesitylphosphino-2-vinylferrocene. It represents a rare example of a FLP where the equilibrium between the open form and the closed internal P/B adduct form is experimentally observable. It also shows a variety of typical FLP reactions, including dihydrogen splitting. The FLPs 8 and 23 (open form) and many precursors and products were characterized by X-ray diffraction.

Internal adduct formation of active intramolecular C4-bridged frustrated phosphane/borane Lewis pairs

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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

 

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Recent developments in design and functionalization of micro- and nanostructural environmentally-sensitive hydrogels based on N-isopropylacrylamide

Synthesis of environmentally-sensitive, and therefore smart hydrogels of micro- and nanosize allowed substantial shortening of time of response of these gels to a change in environmental conditions. This made the hydrogels much more attractive and opened new possibilities of their applications. In this paper we present recent developments in ways of construction of micro- and nanogels, their adaptation to particular needs and possibilities of use. The focus was given to individual, spherical particles and very thin layers of gels on solid supports, including electrodes.

Recent developments in design and functionalization of micro- and nanostructural environmentally-sensitive hydrogels based on N-isopropylacrylamide

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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

 

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Effective Recognition of Different Types of Amino Groups: From Aminobenzenesulfonamides to Amino-(N-alkyl)benzenesulfonamides via Iridium-Catalyzed N-Alkylation with Alcohols

(Chemical Equation Presented). A simple, highly efficient, and general strategy for the direct synthesis of amino-(N-alkyl)benzenesulfonamides has been accomplished via direct N-alkylation of aminobenzenesulfonamides bearing both different types of amino groups with alcohols as alkylating agents. Notably, this research exhibited the potential for the recognition of different types of amino groups in the N-alkylation of complex molecules with alcohols, facilitating the progress of the transition-metal-catalyzed “hydrogen autotransfer (or hydrogen-borrowing) process.”

Effective Recognition of Different Types of Amino Groups: From Aminobenzenesulfonamides to Amino-(N-alkyl)benzenesulfonamides via Iridium-Catalyzed N-Alkylation with Alcohols

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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

 

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pH-Dependent rectification in self-assembled monolayers based on electrostatic interactions

Asymmetric electrostatic interactions dependent on pH between the redox molecules and the terminal group on the top of the self-assembled monolayer (SAM) afford control of the electron transfer property of the SAM having the imidazole terminal group. The Royal Society of Chemistry 2006.

pH-Dependent rectification in self-assembled monolayers based on electrostatic interactions

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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