The Electrochemistry of Hydrocarbons in  HF  / SbF5: Some Mechanistic Conclusions Concerning the Super Acid “Catalyzed” Condensation of Hydrocarbons

Brilmyer, G.H.; Jasinski, Raymond

doi:10.1149/1.2124330

Cited by 83 publications

(7 citation statements)

References 20 publications

(28 reference statements)

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“…These results follow ag eneral trend in accordance with the redox properties of halogens andh alide ions. Thus, as previously demonstrated, [21] SbF 5 act as an oxidanti nH F/SbF 5 solutionsa nd oxidize chloridea nd iodide ions to generate elemental halogen in so-lution. [22] This was confirmed by evidencing the formation of SbI 3 and I 2 by X-ray diffraction analysis of the crude powder collected after reaction of NaI in HF/SbF 5 (see Supporting Information).…”

Section: Entrymentioning

confidence: 63%

Complementary Site‐Selective Halogenation of Nitrogen‐Containing (Hetero)Aromatics with Superacids

Mamontov

Martin‐Mingot

Métayer

et al. 2020

Chemistry A European J

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Site‐selective functionalization of arenes that is complementary to classical aromatic substitution reactions remains a long‐standing quest in organic synthesis. Exploiting the generation of halenium ion through oxidative process and the protonation of the nitrogen containing function in HF/SbF5, the chlorination and iodination of classically inert Csp2−H bonds of aromatic amines occurs. Furthermore, the superacid‐promoted (poly)protonation of the molecules acts as a protection, favoring the late‐stage selective halogenation of natural alkaloids and active pharmaceutical ingredients

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Section: Entrymentioning

confidence: 63%

Complementary Site‐Selective Halogenation of Nitrogen‐Containing (Hetero)Aromatics with Superacids

Mamontov

Martin‐Mingot

Métayer

et al. 2020

Chemistry A European J

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“…Perhaps the most successful and economical method for preparing PPP is the oxidative coupling reaction of benzene reported by Kovacic and co-workers [83][84][85][86][87]. Several electrolytic methods [88][89][90][91][92][93][94] have also been used to prepare polypheneylene. The electrolysis of phenylmagnesium bromide in ether afforded about a 0.1 % yield of polymer [88].…”

Section: Polyphenylenes Poly(p-phenylene)mentioning

confidence: 99%

Conducting Polymers: Concepts and Applications

Mishra

2018

Jour. Atomic Mole. Conden. Nano Phys.

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The developments in the field of electrically conducting polymers have grown very rapidly since the discovery and there is a very sharp increase in conductivity when intrinsically insulating organic conjugated polymers are doped with oxidizing and reducing agents. An overview of technological developments involving conducting polymers clearly indicates that the field expands at unprecedented rates. The manuscript first introduces the conducting polymers (CPs), conducting mechanism, concepts of doping and briefly introduces main applications. Different types of CPs, their unique properties and synthesis is discussed. The present review will help the effective implementation of conducting polymers in different fields, which directly depends on the degree of understanding of their behaviour and properties.properties of the conjugated polymers can be varied to a very large extent by appropriate functionalization. Most extensively studied area of the application of undoped conjugated polymers is the fabrication of the polymeric light-emitting diodes, i.e. electronic devices which exploit the phenomenon of electroluminescence. Electroluminescence of conjugated polymers and more precisely poly(p-phenylene vinylene) was first reported by Burroughes et al. [11] in 1990. These undoped conjugated polymers can also be used in the fabrication of a large variety of other devices like organic field-effect transistors. Polymer LEDs show attractive characteristics, including efficient light generation, with great potential for commercialisation. Again the polymer interests in polymers is in their potential use for rapid, low-cost processing using film-forming polymer solutions. Like the conductive polymers, the semi-conductive polymers obtain their properties from their conduction-molecular orbitals and valence molecular orbitals, i.e., bonding π and antibonding π * orbitals, respectively.In electro-chemical light emitting cells, the semi-conductive polymer could be surrounded asymmetrically with a hole-injection electrode on one side, and a low work function, electron injecting metal contact like aluminum, magnesium, calcium etc. on the other side. The emission of light is then the result of radiative charge carrier recombination in the polymer as electrons from one side and holes from the other recombine.Conducting polymers are conjugated polymers, namely organic compounds that have an extended p-orbital system, through which electrons can move from one end of the polymer to the other. In conjugated polymers, the bonding leads to one unpaired electron (the π-electron) per carbon atom. Moreover, π-bonding, in which the carbon orbitals are in the sp 2 pz configuration and in which the orbitals of successive carbon atoms along the backbone overlap, leads to electron delocalization along the backbone of the polymer. This electronic delocalization provides the "highway" for charge mobility along the backbone of the polymer chain. Electronically conducting polymers are extensively conjugated molecules, and it is believed that they po...

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“…Several previous works have considered replacing strong chemical oxidizers or high temperatures with an electrochemical potential. For example, Brilmyer and Jasinski 33 proposed a methane oxidation process in strong superacids with hydrofluoric acid (HF) and antimony pentafluoride (SbF 5 ). The authors describe a Sb +5 /Sb +3 redox shuttle strategy 33 capable of oxidative coupling of ethane, propane and cycloalkanes; however, methane oxidation was not observed.…”

mentioning

confidence: 99%

“…For example, Brilmyer and Jasinski 33 proposed a methane oxidation process in strong superacids with hydrofluoric acid (HF) and antimony pentafluoride (SbF 5 ). The authors describe a Sb +5 /Sb +3 redox shuttle strategy 33 capable of oxidative coupling of ethane, propane and cycloalkanes; however, methane oxidation was not observed. More recently, Mustain et al 34 and Park et al 35 demonstrated room temperature methane oxidation in aqueous electrolytes at NiO-ZrO 2 or Co 3 O 4 -ZrO 2 electrodes.…”

mentioning

confidence: 99%

Communication—Electrocatalytic Coupling of Methane at Platinum Oxide Electrodes in Superacids

Fang

Arges

et al. 2020

J. Electrochem. Soc.

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Electrochemical oxidation of methane in the absence of chemical oxidants offers the potential to directly synthesize high value hydrocarbons at low temperatures. Experimental results demonstrate methane oxidization at oxidized Pt electrodes in liquid superacid electrolytes. Ethane and ethylene are observed as products under chronoamperometric experiments at room temperature. Faradaic efficiencies for C2 products range from 5% to 25% at anodic potentials between 0.8 to 1.4 V vs RHE. A generalized Lewis-acid Pt2+ mechanism including methylidene coupling is proposed.

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The Electrochemistry of Hydrocarbons in HF / SbF5: Some Mechanistic Conclusions Concerning the Super Acid “Catalyzed” Condensation of Hydrocarbons

Cited by 83 publications

References 20 publications

Complementary Site‐Selective Halogenation of Nitrogen‐Containing (Hetero)Aromatics with Superacids

Complementary Site‐Selective Halogenation of Nitrogen‐Containing (Hetero)Aromatics with Superacids

Conducting Polymers: Concepts and Applications

Communication—Electrocatalytic Coupling of Methane at Platinum Oxide Electrodes in Superacids

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