Reactions of hydroxymethylferrocene. II. Sulfides

Combs, Charles S.; Ashmore, Charles I.; Bridges, Alec F.; Swanson, C. R.; Stephens, William D.

doi:10.1021/jo01257a088

Cited by 14 publications

(3 citation statements)

References 3 publications

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“…Their spectroscopic data have been compared with those reported in the literature, if available. Indeed, complexes 3a , 3g ,15 3b ,16 3c ,17 3e ,10b 3h ,18 and 3i 19 have been previously obtained by different methods. Moreover, the molecular structure of 3b has been determined by X‐ray diffraction.…”

Section: Resultsmentioning

confidence: 99%

“…Direct reactions between ferrocenyl alcohols and thiols mostly concern α‐substituted ferrocenyl alcohols such as [Fc–CH(R)OH] (R = Me, Ph, Fc) 10,11,21. However, it has been reported that 3a and 3g can be obtained by reaction of 1 with thiols in the presence of acetic acid, but the reaction is performed with a large excess of thiol (50 % mixture of water and thiol used as solvent) 15. Interestingly, the catalyst [Fp][OTf] is not inactivated (or “poisoned”) by thiols, although these are potentially able to coordinate to the iron complex 22.…”

Section: Resultsmentioning

confidence: 99%

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Iron‐Catalyzed Ferrocenylmethanol OH Substitution by S, N, P, and C Nucleophiles

et al. 2013

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The iron complex [Fp][OTf] {Fp + = [Fe(CO) 2 (Cp)] + , OTf -= SO 3 CF 3 -} is an efficient catalyst for the direct substitution of the OH group in ferrocenylmethanol [Fc-CH 2 OH] by thiols, aromatic amines, diphenylphosphane, and carbon nucleophiles (furan, pyrrole, and indole). This approach offers a convenient route to ferrocenes containing side chains with [a]3710 different functional groups. The advantages of the method are associated with the use of a catalyst based on iron, which is a nontoxic and readily available transition metal, and in the direct OH substitution, which produces water as the only byproduct.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Iron‐Catalyzed Ferrocenylmethanol OH Substitution by S, N, P, and C Nucleophiles

et al. 2013

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“…(2) all diffusion coefficients are identical (this is reasonable for the dilute solutions used); (3) the direct, heterogeneous oxidation of the sulfidic species does not take place in the potential range considered; (4) the bimolecular reaction between the oxidised mediator and the sulfidic species is ratelimiting, so that the oxidised sulfidic species is at steady-state, enabling the homogeneous bimolecular electron transfer reaction to be considered chemically irreversible; and (5) the outer-sphere, bimolecular, electron transfer reaction is very much faster than competing nucleophilic reactions such as (i) the reaction between FcCH 2 OH and HS À /H 2 S, and (ii) the reaction between chloride ions and the electrogenerated ferricenium derivative -reactions that are known to be slow at room temperature. [17,18] In the calculated voltammograms, since the reaction between the ferricenium species and bisulfide competes with that for H 2 S, an effective rate constant, k eff , was employed for a total sulfur species concentration,…”

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Unravelling the Occurrence of Mediator‐Blood Protein Interactions via the Redox Catalysis of the Physiological Gasotransmitter Hydrogen Sulfide

Ward

Lawrence

et al. 2021

ChemistrySelect

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Ferrocenemethanol is employed as an aqueous, homogeneous redox mediator for hydrogen sulfide. The reaction is seen to follow an EC’ mechanism over the range 6≤pH≤9, with bisulfide reacting four times more rapidly than hydrogen sulfide. In the presence of 10 vol.% hæmolysed blood, greater concentrations of sulfide (as H2S or as HS−) are required to achieve the same degree of redox catalysis, compared with the absence of the blood proteins, at both pH 7 and pH 9. It is suggested that this phenomenon derives from a ferrocenemethanol/blood protein interaction, which is first titrated by the sulfide species. This can give rise to a titration‐based electroanalytical assay for sulfide in blood, whilst being important for blood‐based electrochemical bioassays involving hydrophilic ferrocene derivatives.

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Contributions to the synthesis of some ferrocene‐containing antibiotics

Scutaru¹,

Tǎtaru²,

Mazilu³

et al. 1993

Applied Organom Chemis

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This Review discusses the synthesis and characterization by our Group of new antibiotics belonging to the class of penicillins, cephalosporins and rifamycins with ferrocenyl and 1, 1′‐ferrocenilene residues in the molecule. As reactants for 6‐aminopenicillanic acid (6‐APA) and 7‐aminocephalosporanic acid (7‐ACA) the following were used: 1, 1‐bis(chlorocarbonyl)ferrocene, ferrocenyl sulfochloride, 1, 1′‐ferrocenylenedisulfochloride and thioglycolic acids S‐modified with ferrocene. In the synthesis of rifamycins, the hydrazides of the thioglycolic acids, S‐modified with ferrocene, were employed as nucleophilic agents. The synthesized intermediates were characterized by elemental analysis, TLC, IR, UV and 1H NMR spectra. The characterization of new antibiotics was made by TLC, IR and UV spectral analysis. Biological activity was tested on Gram‐negative and Gram‐positive bacteria. Good activity is reported towards Gram‐positive bacteria in the case of derivatives containing residues of thioglycolic acid S‐modified with ferrocene, the antibacterial activity being similar to that of amoxicillin, carbenicillin and cephalothin. All compounds are inactive towards Gram‐negative bacteria.

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Reactions of hydroxymethylferrocene. II. Sulfides

Cited by 14 publications

References 3 publications

Iron‐Catalyzed Ferrocenylmethanol OH Substitution by S, N, P, and C Nucleophiles

Iron‐Catalyzed Ferrocenylmethanol OH Substitution by S, N, P, and C Nucleophiles

Unravelling the Occurrence of Mediator‐Blood Protein Interactions via the Redox Catalysis of the Physiological Gasotransmitter Hydrogen Sulfide

Contributions to the synthesis of some ferrocene‐containing antibiotics

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