Modern Electroorganic Chemistry

Kyriacou, Demetrios

doi:10.1007/978-3-642-78677-8

Cited by 45 publications

(27 citation statements)

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“…A rough estimate of the state in the frame of this model shows that the electron transfer is too slow to compete with the other deactivation pathways of the excited states. As aliphatic ethers are very poor electron donors [38] this is very unlikely, and therefore we consider that in our case this mechanism is less probable than the H-atom abstraction reaction, in spite of the pronounced acceptor character of MTAD.…”

Section: Discussionmentioning

confidence: 91%

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

et al. 2000

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The photoaddition of 4‐methyl‐1,2,4‐triazoline‐3,5‐dione (4‐MTAD) with a wide variety of acyclic, cyclic and crown aliphatic ethers has been investigated. Monochromatic (λ = 514.5 nm) or polychromatic (λ ≥ 310 nm) irradiations give identical mono‐urazolyl ethers as reaction products. Unsymmetrical acyclic ethers afford a mixture of the two α and α′ mono‐urazolyl ethers. In the case of 12‐crown‐4, mono and di‐substituted products are obtained. ESR experiments and quantum calculations at the AM1 and 6‐31G* levels were performed and a possible reaction mechanism is proposed in which the most probable photochemical process is the H‐abstraction leading to a urazolyl radical.

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Section: Discussionmentioning

confidence: 91%

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

et al. 2000

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“…It is well documented that phenolate ions undergo electrochemical oxidation via one-electron oxidation to phenolate radicals [22]. When generated from unsubstituted phenol, these radicals are known to undergo mainly para-coupling giving rise to linear poly-phenylene oxide [23].…”

Section: Chemical Structure and Morphology Of The Polymeric Eugenolmentioning

confidence: 99%

Preparation and General Properties of Chemically Modified Electrodes Based on Electrosynthesized Thin Polymeric Films Derived from Eugenol

Ciszewski

Milczarek

2001

Electroanalysis

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Eugenol (4‐allyl‐2‐methoxyphenol) was polymerized oxidatively by cyclic voltammetry at platinum and glassy carbon electrodes. It was found that at platinum the polymerization gives rise to a uniform, compact film which could serve as a permselective membrane for analytes of small molecular size. Applications of such films in selective detection of hydrogen peroxide and nitric monoxide were proposed. Monomer oxidation at glassy carbon resulted in less compact films. Interestingly, at higher potentials a porous structure containing large amount of unoxidized o‐methoxyphenyl groups was created. This structure underwent electrochemical demethoxylation leading to the generation of redox active o‐quinone functionalities when the modified electrode was cycled in acidic solution. A small amount of p‐ quinone functionalities was also generated. As could be anticipated the redox couples were capable of mediating electrochemical oxidation of ascorbic acid and NADH. Additionally polymeric eugenol‐coated GC exhibited preconcentration capabilities towards dissolved metal cations. This effect was demonstrated on the electrochemical oxidation of preconcentrated Ce(III) and reduction of Cu(II).

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“…The electrocatalytic properties of nickel hydroxide -Ni(OH) 2 -and oxyhydroxideNiOOH-electrodes, obtained in alkaline medium under anodic polarization conditions, have been explored extensively for the oxidation of aliphatic and aromatic alcohols and amino compounds via the participation of Ni(III) species [1,3,4,[13][14][15][16][17][18][19][20][21][22]. In contrast, few studies have focused on the performance of Ni(OH) 2 /NiOOH couples in the electrooxidation of unsaturated alcohols (i.e., alken-1-ols or alkyn-1-ols) [1,3,23].…”

Section: Introductionmentioning

confidence: 99%

Electrocatalytic activity of Ni-doped nanoporous carbons in the electrooxidation of propargyl alcohol

García‐Cruz

Sáez

Ania

et al. 2014

Carbon

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Please cite this article as: García-Cruz, L., Sáez, A., Ania, C.O., Solla-Gullón, J., Thiemann, T., Iniesta, J., Montiel, V., Electrocatalytic activity of Ni-doped nanoporous carbons in the electrooxidation of propargyl alcohol, Carbon (2014), doi: http://dx.doi.org/10.1016/j.carbon. 2014.02.066 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Ni-doped nanoporous carbons provided similar propargyl alcohol conversions for very low metallic contents. Nanoparticulated Ni on various carbon supports gave rise to the highest electrocatalytic activity in terms of product selectivity, with a clear dependence on Ni content. The results point to the importance of controlling the dispersion of the Ni phase within the carbon matrix for a full exploitation of the electroactive area of the metal. Additionally, a change in the mechanism of the propargyl alcohol electrooxidation was noted, which seems to be related to the physicochemical properties of the carbon support as well. Thus, the stereoselectivity of the electrooxidative reaction can be controlled by the active nickel content immobilized on the anode, with a preferential oxidation to (Z)-3-(2-propynoxy)-2-propenoic acid with high Ni-loading, and to propiolic acid with low loading of active Ni sites. Moreover, the formation of (E)-3-(2-propynoxy)-2-propenoic acid was discriminatory irrespective of the experimental conditions and Ni loadings on the carbon matrixes.

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Modern Electroorganic Chemistry

Cited by 45 publications

References 0 publications

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

Preparation and General Properties of Chemically Modified Electrodes Based on Electrosynthesized Thin Polymeric Films Derived from Eugenol

Electrocatalytic activity of Ni-doped nanoporous carbons in the electrooxidation of propargyl alcohol

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