Brief introduction of C14H19FeN

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Classical synthetic approach to highly enantiomeric-enriched ferrocenes relies on the formation of their conjugates with (R,R)-tartaric acid. Herein, the quantum chemical calculations based on X-ray data as an initial approximation, were carried out for both (R)- and (S)-diastereomers of N,N-(dimethyl-1-ferrocenyl)ethylamine (Ugi’s amine) with (R,R)-tartaric acid. A high correlation between the experimental data and the calculated Gibbs free energies values of solvation was obtained. Based on the advanced DFT calculations, the chemical aspects of the separation of the diastereomeric complexes of (R)- and (S)-FcCH(CH3)N(CH3)2 with (R,R)-tartaric acid were clarified. Quantum chemical calculations made it possible to justify the use of methanol as a solvent in the successful separation of the diastereomeric complexes of the Ugi’s amine. This mathematical approach can be used in practice to separate racemates of other bioactive ferrocene compounds, for example, ferrocenyl alkyl azoles.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

New explortion of C14H19FeN

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A molecular mechanics force field has been developed for the conformational analysis of amido- and aalpha-aminoferrocenes. Parameterization for ring-substituent rotational barriers in amidoferrocenes and other cross-conjugated derivatives have been calculated using DFT on both the free and complexed cyclopentadienyl ligand. Modeled structures of (diisopropylamido)- and (dimethylamido)ferrocene and N,N-dimethyl-alpha-ferrocenylethylamine are in agreement with those determined through single-crystal X-ray diffraction. The diastereo-selective lithiation of N,N-dimethylferrocenylethylamine and sparteine-mediated enantio-selective lithiation of (diisopropylamido)ferrocene using MeLi have been modeled through an assumed reversible adduct formation at the amine nitrogen or amide oxygen, followed by an irreversible ring lithiation. Results indicate that selectivity results from ring lithiation via the adduct conformer with the shortest C-Hring- – -H3C-Li interaction.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Archives for Chemistry Experiments of 31886-57-4

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The synthesis of primary, secondary, and tertiary ferrocenylethylamines

A simplified procedure for the preparation of alpha-N,N-dialkylaminoethylferrocenes R2NR’ (r=Me, C6H11, CHMe2; R’=CH(CH3)C5H4FeC5H5) from the alcohol R’OH by treatment with HBr and R2NH is described.Use of ammonia results in the isolation of R’NH2, R’2NH (major product) and R’3N and use of the optically active amine d-(+)-H2NCH(CH3)C6H5 gives rise to diastereomers R’NHCH(CH3)C6H5 which are separable.When diphenylphosphine is substituted for an amine the oxide R’P(O)Ph2 is obtained in low yield.The secondary amine R’2NH reacts with n-butyllithium and chlorodiphenylphosphine to afford R’2NHPPh2.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

New explortion of (S)-N,N-Dimethyl-1-ferrocenylethylamine

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Reference of 31886-57-4, In some cases, the catalyzed mechanism may include additional steps. Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. 31886-57-4, Name is (S)-N,N-Dimethyl-1-ferrocenylethylamine,introducing its new discovery.

Asymmetric [3+2]-Cycloaddition of Morita-Baylis-Hillman Carbonates with Maleimides Catalyzed by Chiral Ferrocenylphosphines

New chiral ferrocenylphosphines LB1-LB9 were designed and prepared through simple synthetic approaches. These air-stable ferrocenylphosphines were applied to promote asymmetric [3+2]-cycloaddition of Morita-Baylis-Hillman carbonates with maleimides, among which LB7 was shown to have good catalytic activity to afford the corresponding multifunctional cyclopentenes in up to 59% yield and up to 53% ee under mild reaction conditions. A plausible reaction mechanism was proposed.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

New explortion of 31886-57-4

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Determination of the enantiomeric composition of N,N-dimethyl-alpha-ferrocenylethylamine by 1H NMR spectroscopy

A new method for the determination of enantiomeric composition of N,N-dimetriyl-alpha-ferrocenylethylamine by 1H NMR spectroscopy using (S)-mandelic acid as a chiral protonating agent was proposed.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Top Picks: new discover of (S)-N,N-Dimethyl-1-ferrocenylethylamine

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Potential-driven chirality manifestations and impressive enantioselectivity by inherently chiral electroactive organic films

The typical design of chiral electroactive materials involves attaching chiral pendants to an electroactive polyconjugated backbone and generally results in modest chirality manifestations. Discussed herein are electroactive chiral poly-heterocycles, where chirality is not external to the electroactive backbone but inherent to it, and results from a torsion generated by the periodic presence of atropisomeric, conjugatively active biheteroaromatic scaffolds, (3,3-bithianaphthene). As the stereogenic element coincides with the electroactive one, films of impressive chiroptical activity and outstanding enantiodiscrimination properties are obtained. Moreover, chirality manifestations can be finely and reversibly tuned by the electric potential, as progressive injection of holes forces the two thianaphthene rings to co-planarize to favor delocalization. Such deformations, revealed by CD spectroelectrochemistry, are elastic and reversible, thus suggesting a breathing system. A jolt upon recognition: Torsion in the electroactive backbone endows poly-heterocycle films with high chiroptical activity, which is reversibly tunable by the electric potential, and outstanding enantiorecognition capability with about 100 mV between two enantiomeric ferrocenyl amino probes, in any order, in alternating sequences, and as a racemate.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Brief introduction of 31886-57-4

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In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. Formula: C14H19FeN, Name is (S)-N,N-Dimethyl-1-ferrocenylethylamine, belongs to chiral-nitrogen-ligands compound, is a common compound. Formula: C14H19FeNCatalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In an article, authors is Khozeimeh Sarbisheh, Elaheh, once mentioned the new application about Formula: C14H19FeN.

Insight into the Thermal Ring-Opening Polymerization of Phospha[1]ferrocenophanes

A mixture of cis/trans isomers of phospha[1]ferrocenophanes equipped with one iPr group at the alpha position to the bridging PhP moiety was prepared. Both isomers (cis-4 and trans-4) were obtained as racemates and could be separated so that their thermal properties were investigated individually. The molecular structure of cis-4 was determined by single-crystal X-ray analysis showing a tilt angle alpha=26.35(8). Interconversion between both isomers occurred in the melt at elevated temperatures and revealed that the trans isomer is thermodynamically more stable. Structural and thermodynamic data was complemented by DFT calculations (B3PW91/6-311+G(d,p) and B3PW91-D3(BJ)/6-311+G(d,p)). Performance of thermal ring-opening polymerization (ROP) of trans-4 at 230 C gave polymers and cyclic oligomers. Gel permeation chromatography (GPC) of the sulfurized polymer resulted in a molecular weight of 62.5 kDa (Mw) and a polydispersity index of 1.39 (PDI). Mass spectrometric analysis of the oligomers showed the presence of cyclic species from dimers to heptamers. After sulfurization, preparative thin layer chromatography led to the separation of three isomeric dimers. Structural characterization of these dimers by single-crystal X-ray analysis led to the conclusion that the Fe?Cp bond breaks during the thermal ROP process. A mechanism similar to the known mechanism of the photolytic ROP of ferrocenophanes is proposed.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Final Thoughts on Chemistry for C14H19FeN

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Related Products of 31886-57-4, 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. 31886-57-4, Name is (S)-N,N-Dimethyl-1-ferrocenylethylamine, molecular formula is C14H19FeN. In a Patent£¬once mentioned of 31886-57-4

A Ugi’s amine and synthetic method of derivative thereof (by machine translation)

The invention discloses a formula (I) indicated by the Ugi’s amine and its derivatives of the synthesis method, the method to ferrocene and its derivatives as raw materials, obtained by reductive amination of racemic […], then racemic […] split by the resolving agent, to a primary amine of the optical isomer, optical isomer primary amine by alkylation or reductive amination reaction shall be stated Ugi’s amine and its derivatives. The chiral Ugi’s amine and its derivatives can be used for synthesizing a series of Josiphos such ferrocene diphosphine ligand, as various metal complex catalyst of chiral ligand, is preparing a pharmaceutical intermediate, agricultural chemicals important chiral catalyst ligand, in metal catalytic asymmetric reaction have a wide range of application, and is suitable for industrial scale production. The invention mild reaction conditions, cheap raw material, the synthetic route is simple, higher yield and chiral purity. (by machine translation)

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Awesome Chemistry Experiments For 31886-57-4

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One-pot alpha-ferrocenylalkylation of amines and alcohols with alpha-ferrocenyl substituted alcohols under acid-free conditions

One-pot reaction of FcCH(R)OH with equimolar quantities of BunLi and EtOCOCl followed by an excess of amine produces N-(alpha-ferrocenylalkyl)amines in up to 98% yields. Nitrogen heteroaryl amines undergo the alpha-ferrocenylalkylation at the amino group. The alpha-ferrocenylalkylation of alcohols and phenols (R’OH) leads to a formation of ethers FcCH(R)OR? in lower yields. The reactions proceed via an intermediate formation of alpha-ferrocenylalkyl carbonates FcCH(R)OCOOEt. The side reactions associated with this protocol are discussed.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Discovery of (S)-N,N-Dimethyl-1-ferrocenylethylamine

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Thermal ring-opening polymerization of planar-chiral Sila[1]ferrocenophanes

The new Me2Si-bridged [1]ferrocenophane ([1]FCP) with one iPr group in alpha position on a Cp ring was synthesized in an enantiopure (Sp-4) and a racemic form (rac-4). The molecular structure of rac-4 was determined by single-crystal X-ray analysis (tilt angle alpha = 20.15(14)). Experimental and calculated molecular structures of the related [1]FCPs with one (Sp-4 and rac-4) or two iPr groups (Sp,Sp-4) are compared to that of the nonsubstituted [1]FCP Me2Sifc. Differential scanning calorimetry (DSC) measurements resulted in HROP of 72(¡À2) kJ mol-1 for rac-4 and 62(¡À2) kJ mol-1 for the known Sp,Sp-4. While thermal ring-opening polymerization of Sp,Sp-4 gave insoluble material, the monosubstituted monomers Sp-4 and rac-4 resulted in soluble polymers with molecular weights (Mw) of 5.3 ¡Á 106 and 2.6 ¡Á 106 Da, respectively. Investigation of the polymer structures by 29Si NMR spectroscopy gave further evidence that the breakage of Si-Cp bonds occurs in the thermal ROP process of sila[1]ferrocenophanes.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis