Electrochemical production of initiators for polymerization processes

Silvestri, Guido; Gambino, Salvatore; Filardo, Giuseppe

doi:10.1007/3-540-10217-5_2

Cited by 21 publications

(5 citation statements)

References 94 publications

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“…The data obtained are presented in Table 3, from which it follows that the highest amino acid yields were obtained on zinc and glassy carbon among the cathodes employed when conducting preparative electrolysis. Similar results were obtained by Silvestri et al [14] in the electrochemical carboxylation of unsubstituted benzalaniline on Zn and GC electrodes. One reason for the varying amino acid yields on cathodes of the different materials could be the singularities of the imines' adsorption on them which effects on subsequent electrochemical and chemical processes.…”

Section: Effect Of the Cathode Materials On The N-phenylphenylglycine supporting

confidence: 91%

“…The possibility of forming similar dimers has been shown in Refs. [13,14] in the case of some imines, that does not contain fluorine atoms. The similar dimers can be formed in the case of electrochemical reduction of fluorocontaining imines that confirm with results of chromatography-mass spectrometry study of the products of preparative electrolysis of imine 1 (cathode, GC; anode, Al; Bu 4 NBr, DMF).…”

Section: Electrochemical Activation Of Fluorocontaining Iminesmentioning

confidence: 98%

“…In particular, electrochemically activated introduction of CO 2 to the C N bond can result in a-amino acids [13,14].…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical carboxylation of fluorocontaining imines with preparation of fluorinated N-phenylphenylglycines

Koshechko

Titov

Bondarenko

et al. 2008

Journal of Fluorine Chemistry

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Section: Effect Of the Cathode Materials On The N-phenylphenylglycine supporting

confidence: 91%

Section: Electrochemical Activation Of Fluorocontaining Iminesmentioning

confidence: 98%

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Electrochemical carboxylation of fluorocontaining imines with preparation of fluorinated N-phenylphenylglycines

Koshechko

Titov

Bondarenko

et al. 2008

Journal of Fluorine Chemistry

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“…Monocarboxylates and/or dicarboxylates have thus been obtained from activated olefins and polycyclic aromatic hydrocarbons . N-heteroaromatic molecules similarly yield the corresponding dihydrocarboxy derivatives while α-hydroxy and α-amino acids are produced from carbonyl compounds and imines, respectively …”

mentioning

confidence: 99%

Homogeneous Electron Transfer Catalysis of the Electrochemical Reduction of Carbon Dioxide. Do Aromatic Anion Radicals React in an Outer-Sphere Manner?

et al. 1996

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Electrochemically generated anion radicals of aromatic nitriles and esters possess the remarkable property to reduce carbon dioxide to oxalate with negligible formation of carboxylated products. They may thus serve as selective homogeneous catalysts for the reduction of CO 2 in an aprotic medium. The catalytic enhancement of the cyclic voltammetric peaks of these catalysts is used to determine the rate constant of the electron transfer from these aromatic anion radicals to CO 2 as a function of the catalyst standard potential. Substituted benzoic esters allowed a particularly detailed investigation of the resulting activation-driving force relationship. Using 14 different catalysts in this series made it possible to finely scan a range of reaction standard free energies of 0.4 eV. Detailed analysis of the resulting data leads to the conclusion that the reaction is not a simple outer-sphere electron transfer. It rather consists in a nucleophilic addition of the anion radical on CO 2 , forming an oxygen (or nitrogen for the nitriles)carbon bond, which successively breaks homolytically, generating the parent ester (or nitrile) and the anion radical of CO 2 , which eventually dimerizes to oxalate.

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“…Electrochemical carboxylation of imine derivatives is known to gives α‐amino acids [44–46] . However, only N ‐phenyl imines derived from benzaldehydes were used as substrates [44,45] and transformation of an N ‐phenyl group to N ‐H derivatives is generally difficult. The poor yield of α‐amino acids in the reaction of imines derived from aliphatic aldehydes [46] is also problematic.…”

Section: Electrochemical Carboxylation Of Organic Compoundsmentioning

confidence: 99%

Electrochemical Fixation of Carbon Dioxide: Synthesis of Carboxylic Acids

Senboku

2021

The Chemical Record

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In the past three decades, we have focused on the fixation of carbon dioxide by electrochemical method with a carbon‐carbon bond forming reaction to yield carboxylic acid, so‐called electrochemical carboxylation. Vinyl bromides and triflates, difluoroethylbenzenes, polyfluoroarenes, benzal diacetates, phenyl‐substituted alkenes and enamides, and α‐aminosulfones were found to be effective as substrates for electrochemical carboxylation. Phenylacetic acids and phenylpropanoic acids including non‐steroidal anti‐inflammatory agents and their fluorinated analogues, polyfluorobenzoic acids, mandel acetates, and α‐ and β‐amino acids were successfully synthesized. Electrochemical double carboxylation of dibenzyl carbonates, reuse of carbon dioxide in benzyl carbonates for fixation of carbon dioxide (recycle‐electrochemical carboxylation), sequential aryl/vinyl radical cyclization‐electrochemical carboxylation, sacrificial anode‐free electrochemical carboxylation, and the use of supercritical carbon dioxide both as a reaction media and a reagent were also developed. In this personal account, our efforts in and results of electrochemical fixation of carbon dioxide to organic compounds with carbon‐carbon bond forming reactions yielding novel and useful carboxylic acids are introduced along with their applications and some new results.

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Electrochemical production of initiators for polymerization processes

Cited by 21 publications

References 94 publications

Electrochemical carboxylation of fluorocontaining imines with preparation of fluorinated N-phenylphenylglycines

Electrochemical carboxylation of fluorocontaining imines with preparation of fluorinated N-phenylphenylglycines

Homogeneous Electron Transfer Catalysis of the Electrochemical Reduction of Carbon Dioxide. Do Aromatic Anion Radicals React in an Outer-Sphere Manner?

Electrochemical Fixation of Carbon Dioxide: Synthesis of Carboxylic Acids

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