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Mono and difunctionalisation of chiral ferrocenyl bis-acetals. X-Ray crystal structure of bis-1,1?-[(2S, 4S)-(hydroxymethyl)-2-dioxane1,3]-ferrocene

The chiral 1,1?-bis-acetals, bis-1,1?-[(2S, 4S)-(hydroxymethyl)-2-dioxane1,3]-ferrocene (3) and 1,1?-bis-1,1?-[(2S, 4S)-(methoxymethyl)-2-dioxane1,3]-ferrocene (4) were synthesized. (3) was crystallographically characterised. The ortholithiation of (4) was studied in various conditions. Fair yields of monosubstituted compounds could be obtained with a complete regioselectivity in favor of the 2 position but the diastereoselectivities were moderate (up to 35%). Some disubstituted compounds can be isolated but in low yields (up to 8%). The regioselectivity is complete in favor of the 2,2?-disubstituted isomer. Only the diastereoisomer with two opposite planar chiralities is observed.

Mono and difunctionalisation of chiral ferrocenyl bis-acetals. X-Ray crystal structure of bis-1,1?-[(2S, 4S)-(hydroxymethyl)-2-dioxane1,3]-ferrocene

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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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The synthesis and properties of bis-1,1?-(porphyrinyl)ferrocenes

Ferrocene-bridged bisporphyrins have been synthesized by the condensation of corresponding dipyrromethane-derived diols with a bisdipyrromethane. Purification of the final compounds has been achieved without chromatography. The specific geometry of these bisporphyrins makes them valuable starting points for building complex molecular and supramolecular structures. In particular it provides a core to which multiple sites of attractive intermolecular interactions can be attached thereby creating compounds predisposed to form complex networks by association. We have studied the structure of bis-1,1?-(porphyrinyl)ferrocenes by 1H NMR, UV-Vis and electrochemistry. Results have shown that complex dynamic processes occur in these molecules (which may involve conformers, formation of H-aggregates and tautomers) and that they have non-typical electrochemical behaviour. The Royal Society of Chemistry 2005.

The synthesis and properties of bis-1,1?-(porphyrinyl)ferrocenes

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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 hydrolysis of [alkenyl(alkoxy)carbene]manganese complexes: Evidence for a transient allylic intermediate on the way to alpha,beta-unsaturated aldehydes

A variety of alkenylcarbene complexes [Cp'(CO)2Mn= C(OEt)CH=CHR] (3) (Cp’ = TiS-MeCsH4) was obtained in a straightforward manner upon aldol condensation of [Cp'(CO)2Mn=C(OEt)CH3] (1) with aromatic and alpha,beta- unsaturated aldehydes RC(H)O (2). The reaction is totally stereoselective, giving (E)- or (all-E)-alkenylcarbenes only. The protonation of 3 at low temperature followed by reaction with water affords the alpha,beta-unsaturated aldehyde complexes [Cp'(CO)2Mn(n2-RCH=CHCHO] (5), from which the aldehydes RC(H)=C(H)C(H)O (6) were displaced by acetonitrile. The intermediate aldehyde complexes are shown to result from the hydrolysis of a transient cationic pi- allyl species [Cp'(CO)2Mn(n3-RCHCHC(OEt)H]+ ([4]+) formed upon protonation of 3.

Synthesis and hydrolysis of [alkenyl(alkoxy)carbene]manganese complexes: Evidence for a transient allylic intermediate on the way to alpha,beta-unsaturated aldehydes

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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

 

Properties and Exciting Facts About 1,1′-Ferrocenedicarboxaldehyde

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One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, name: 1,1′-Ferrocenedicarboxaldehyde, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 1271-48-3, Name is 1,1′-Ferrocenedicarboxaldehyde, molecular formula is C12H10FeO2

Selective functionalization of the 1?-position in ferrocenecarbaldehyde

An efficient and selective new method for the preparation of unsymmetrical 1,1?-disubstituted ferrocenes by a one-pot procedure, starting from ferrocenecarbaldehyde, is disclosed.

Selective functionalization of the 1?-position in ferrocenecarbaldehyde

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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 characterisation of the new diaza ferrocene macrocycle 1,1?-( 2,6-diazahepta-1,6-diene) ferrocene and its parent amine 1,1?-( 2,6-diazaheptane ) ferrocene

Reaction of ferrocene-1,1?-dicarbaldehy de and propylenediamine yields the Schiff-base derivative 1,1?-(2,6-diazahepta-1,6-diene)-ferrocene (1). The molecular structure of 1 has been determined by single crystal X-ray analysis. It crystallises in the monoclinic system, space group P21/c, a=13.507(3), b=9.800(2), c=10.086(2) A, beta=110.81(3), Z=4 and V=1248.0(5) A3. Refinement of the atomic parameters by least-squares techniques gave a final R factor of 0.074 for 1588 observed reflections having 1>2sigma(1), Hydrogenation of 1 with LiA1H4 results in the parent amine 1,1?-(2,6-diazaheptane)ferrocene (2). The protonation of 2 has been investigated by potentiometry in water in the pH range 11-6. At pH lower than 6, 2 is unstable in solution. The E1/2 potential for 2 is pH-dependent (E1/2(pH 11) = 255, E1/2(pH 6) =435 mV). A similar behaviour was also observed in THF:water (60:40 vol./vol.). The electrochemical behaviour for 1 and 2 has also been studied in CH2Cl2.

Synthesis and characterisation of the new diaza ferrocene macrocycle 1,1?-( 2,6-diazahepta-1,6-diene) ferrocene and its parent amine 1,1?-( 2,6-diazaheptane ) ferrocene

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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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Ferrocene substituted nitronyl nitroxide and imino nitroxide radicals. Synthesis, X-ray structure and magnetic properties

The synthesis, X-ray structure and magnetic properties of two new ferrocene substituted nitroxide monoradicals are described. The magnetic susceptibility data was nicely fitted in both cases to the Curie-Weiss law yielding the Weiss constants of theta=-1.8 and -1.1 K for radicals 1 and 2, respectively. This result evidenced the presence of very weak antiferromagnetic intermolecular interactions between neighbor molecules. Moreover, the X-ray structure of the key precursor 2,3-bis(hydroxyamino-)-2,3-dimethylbutane (3) is also included.

Ferrocene substituted nitronyl nitroxide and imino nitroxide radicals. Synthesis, X-ray structure and magnetic 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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Some insights into the gold-catalysed A3-coupling reaction

A series of cyclometallated and functionalised NHC gold(I) and gold(III) complexes, many of which feature chiral ligands, and their application to A3-coupling reactions is presented. Gold(III) complexes were found to be particularly effective catalysts for the coupling in a range of solvents, however no asymmetric induction was obtained when using chiral gold complexes and the rate of product formation was found to be similar even when using different ligand systems. In-situ NMR analysis of these reactions indicates that decomposition of the catalyst occurs during the course of the reaction while TEM studies revealed the presence of gold nanoparticles in crude reaction mixtures. Taken together these data suggest that the gold nanoparticles, rather than the intact gold complexes, could be the catalytically active species, and if so this may have significant implications for other gold-catalysed systems.

Some insights into the gold-catalysed A3-coupling reaction

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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 third-order nonlinear optical properties of symmetrical ferrocenyl Schiff base materials

Six symmetrical ferrocenyl Schiff base materials were synthesized and characterized by UV, 1H NMR, mass spectrometry (MS) and elemental analysis. Their off-resonant third-order nonlinear optical properties were measured using femtosecond laser and degenerate four-wave mixing (DFWM) technique. The third-order nonlinear optical susceptibilities chi(3) were 1.961-6.363 ¡Á 10-13 esu. The nonlinear refractive indexes n2 were 3.609-11.716 ¡Á 10-12 esu. The second-order hyperpolarizabilities gamma of these molecules were 1.967-6.388 ¡Á 10-31 esu. The response time were 45.759-73.079 fs. The results indicate that these materials have potential nonlinear optical applications.

Synthesis, characterization and third-order nonlinear optical properties of symmetrical ferrocenyl Schiff base materials

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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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Tuning of the electrochemical recognition of substrates as a function of the proton concentration in solution using pH-responsive redox-active receptor molecules

Reaction of ferrocene-1,1′-dicarbaldehyde and ethane-l,2-diamine yielded the Schiff-base derivative 2,5,19,22-tetraaza<6.6>(1,1′)ferrocenophane-1,5-diene, 1 the molecular structure of which has been determined by singlecrystal X-ray analysis.Hydrogenation of 1 with LiAIH4 resulted in the corresponding amine 2,5,19,22-tetraaza<6.6>(1,1′)ferrocenophane 2 which was characterised crystallographically.The protonation behaviour of 2 (denoted as L) and its complex formation with copper(II), nickel(II) and zinc(II) has been studied by potentiometric titrations in tetrahydrofuran-water (70:30 v/v) (0.1 mol dm-3 NBu4ClO4, 25 deg C).The complexes 3+, 2+, + and are formed.An electrochemical study of compound 2 has also been performed under the same conditions at which the potentiometry was carried out and the pKa values for the mixed-valence Fe(II)Fe(III) and oxidised Fe(III)Fe(III) species determined by fitting the curve of E1/2 versus pH.From those data the Pourbaix diagram of the redox-active 2 has been calculated.Compound 2 can be considered as a selective electrochemical sensor for copper(II).

Tuning of the electrochemical recognition of substrates as a function of the proton concentration in solution using pH-responsive redox-active receptor molecules

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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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Ferrocene derivatives and its synthetic method and application (by machine translation)

The present invention provides two ferrocene pyridine derivative and its synthesis method, wherein ferrocene single arm pyridine derivatives FeL1 and ferrocene double-arm pyridine derivatives FeL2 can be used for Cu2 + And Cr3 + Detection. (by machine translation)

Ferrocene derivatives and its synthetic method and application (by machine translation)

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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