Trifluoromethanesulfonic Acid

Subramanian, L. R.; Martı́nez, Antonio Garcı́a; Hanack, Michael; Prakash, G. K. Surya; Hu, Jinbo

doi:10.1002/047084289x.rt246.pub2

Cited by 6 publications

(9 citation statements)

References 95 publications

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“…Triflate 3g showed higher catalytic activity than tetrafluoroborate 3h , most likely because trifluoromethanesulfonic acid released during the first step of the catalytic cycle is fully dissociated due to its high acidity (in contrast to tetrafluoroboric acid), thus maximally supporting the specific acid catalyzed elimination (cf. Scheme ) …”

Section: Resultsmentioning

confidence: 99%

Electron-Deficient Heteroarenium Salts: An Organocatalytic Tool for Activation of Hydrogen Peroxide in Oxidations

et al. 2015

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A series of monosubstituted pyrimidinium and pyrazinium triflates and 3,5-disubstituted pyridinium triflates were prepared and tested as simple catalysts of oxidations with hydrogen peroxide, using sulfoxidation as a model reaction. Their catalytic efficiency strongly depends on the type of substituent and is remarkable for derivatives with an electron-withdrawing group, showing reactivity comparable to that of flavinium salts which are the prominent organocatalysts for oxygenations. Because of their high stability and good accessibility, 4-(trifluoromethyl)pyrimidinium and 3,5-dinitropyridinium triflates are the catalysts of choice and were shown to catalyze oxidation of aliphatic and aromatic sulfides to sulfoxides, giving quantitative conversions, high preparative yields and excellent chemoselectivity. The high efficiency of electron-poor heteroarenium salts is rationalized by their ability to readily form adducts with nucleophiles, as documented by low pKR+ values (pKR+ < 5) and less negative reduction potentials (Ered > -0.5 V). Hydrogen peroxide adducts formed in situ during catalytic oxidation act as substrate oxidizing agents. The Gibbs free energies of oxygen transfer from these heterocyclic hydroperoxides to thioanisole, obtained by calculations at the B3LYP/6-311++g(d,p) level, showed that they are much stronger oxidizing agents than alkyl hydroperoxides and in some cases are almost comparable to derivatives of flavin hydroperoxide acting as oxidizing agents in monooxygenases.

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Section: Resultsmentioning

confidence: 99%

Electron-Deficient Heteroarenium Salts: An Organocatalytic Tool for Activation of Hydrogen Peroxide in Oxidations

et al. 2015

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“…For samples #1 to #6, the precipitation took place in an environment with a very high acidity. Highly concentrated triflic acid solutions and its salts are often hygroscopic [25,26]. Indeed, the thorium oxalate obtained at such conditions is not the typically observed hexahydrate [14], but a dihydrate (see Fig.…”

Section: Precipitation Of Thorium(iv) Oxalate From Triflic Acid Solutmentioning

confidence: 99%

Studies on the Thoria Fuel Recycling Loop Using Triflic Acid: Effects of Powder Characteristics, Solution Acidity, and Radium Behavior

Tyrpekl

Lommelen

Wangle

et al. 2019

J. Sustain. Metall.

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A convenient recycling loop is one of the key factors that will help to implement the thorium-based nuclear fuel cycle in the future. Herein, a study is presented concerning the recycling loop of thoria production scrap using dissolution with trifluoromethanesulfonic (triflic) acid and recovery by precipitation with oxalic acid. The kinetics of thoria powders and pellet dissolution was assessed and compared with the THOREX process. The effect of the triflic acid concentration on the recovery yield of thorium during oxalate precipitation was examined, as well as the behavior of radium during this reaction. Finally, the effect of the triflic acid concentration on the recovered thoria morphology was investigated. The triflic acid has minimal effect on the recovery yield during oxalate precipitation even in the case of high acid concentrations. In general, the solubility of radium(II) oxalate is higher than for thorium(IV) and has a maximum at a triflic acid solution of 4 M. An interesting observation was that a stable dihydrate of thorium(IV) oxalate is formed in solution of high triflic acid concentration. It might be explained by the hygroscopic medium during precipitation of the oxalate. All above mentioned observations confirm the benefits of usage of the triflic acid-based closed recycling loop for thorium dioxide-based nuclear fuel.

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“…62 However, a few examples in acidic media are known too. 63 Purification of the triflic acid by distillation over triflic anhydride 64 reduced the reaction time to 2 h at r. t., but also resulted in the formation of the demethylated derivative 15 as a sideproduct.…”

Section: Synthesismentioning

confidence: 99%

2,5-Diaryl 6-hydroxyphenalenones for Single-Molecule Junctions

et al. 2022

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A modular access to 2,5-diaryl 6-hydroxyphenalenone derivatives is developed and demonstrated by a small series of 5 molecules. Within this series, the structures 1 and 2 expose terminal methylsulfanyl anchor groups, enabling their integration in a single molecule junction. The modular synthesis is based on Suzuki cross coupling of the aryl substituents as boronic acid precursors with 5,8-dibromo-2-(tert.butyl)-4,9-dimethoxy-2,3-dihydro-1H-phenalen-1-one, and the subsequent transformation of the product to the desired 2,5-diaryl 6-hydroxyphenalenone in a reduction/deprotection sequence. The new structures are fully characterized and their optical and electrochemical properties are analysed. For the derivatives 1 and 2 suitable for single molecule junctions, the corresponding oxophenalenoxyl radicals 1R and 2R were obtained by oxidation and analysed by EPR-spectroscopy. Preliminary mechanical break junction experiments with 1 display the structure’s ability to form transient single molecule junctions. The intention behind the molecular design is to profit from the various redox states of the structure (including the neutral radical) as molecular switch in an electro-chemically triggered single molecule transport experiment.

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Trifluoromethanesulfonic Acid

Cited by 6 publications

References 95 publications

Electron-Deficient Heteroarenium Salts: An Organocatalytic Tool for Activation of Hydrogen Peroxide in Oxidations

Electron-Deficient Heteroarenium Salts: An Organocatalytic Tool for Activation of Hydrogen Peroxide in Oxidations

Studies on the Thoria Fuel Recycling Loop Using Triflic Acid: Effects of Powder Characteristics, Solution Acidity, and Radium Behavior

2,5-Diaryl 6-hydroxyphenalenones for Single-Molecule Junctions

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