Trifluoromethanesulfonic acid and derivatives

Howells, Richard D.; Cown, J. D. Mc

doi:10.1021/cr60305a005

Cited by 395 publications

(202 citation statements)

References 62 publications

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“…Agreement with the observed behaviour comes from spectroscopic and kinetic studies related to equilibria and reactivity of TFMSA [27][28][29]31]. It is also well known that HNO 3 and CF 3 SO 3 H, in the reaction between the pure reagents, combine to form a solid identified as a mixture of CF 3 …”

Section: Acid-catalysed Reactionssupporting

confidence: 60%

“…Trifluoromethanesulfonic acid (TFMSA or triflic acid) is known to be a strong acid suitable to be used as catalyst for synthetic applications [1][2][3][4][5][6][7][8][9]. The design of acid-catalysed reactions over solids has caused a pronunced need for further researchs in this area and supported triflic acid [10][11][12][13][14] or materials with -CF 2 SO 3 H groups [9,[15][16][17][18] are becoming now available to replace homogeneous acid solutions.…”

Section: Introductionmentioning

confidence: 99%

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Acidity and reactivity of trifluoromethanesulfonic acid in liquid and solid acid catalysts

Marziano

Ronchin

Tortato

et al. 2001

Journal of Molecular Catalysis A: Chemical

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The acidic properties of CF 3 SO 3 H/SiO 2 acid catalysts have been investigated by the protonation of weak bases (B) (B+H + BH + ) and the proton-transfer process from (H + A − ) to (BH + A − ) has been analysed by a thermodynamic procedure used to account the variation of the activity coefficient terms of the species involved. Acid-base systems with different substituted pyridines as back-titrating agents of BH + (i.e. BH + → B) have also been studied and the changes observed in the acid-base interactions according to basicity of pyridines are discussed. The results in solid phase have been compared with those observed in concentrated aqueous solutions (i.e. CF 3 SO 3 H + H 2 O) where "acidity" and "protonating ability" have been distinguished as parameters of interest in the description of nonideal acid systems.Silica loaded with CF 3 SO 3 H, with H 2 SO 4 and with a mixture of both acids have been tested in acid catalysed reactions and their catalytic effectiveness has been explored towards substrates with high acid requirements for the conversion reagents-products. From the available observations in liquid and in solid phase, CF 3 SO 3 H has been proved to be a less effective acid catalyst than expected from the observed protonating ability of acidic medium. Strong interactions between ionic species and the involvement of ion-pairs in concentrated acid systems have been suggested.

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Section: Acid-catalysed Reactionssupporting

confidence: 60%

Section: Introductionmentioning

confidence: 99%

Acidity and reactivity of trifluoromethanesulfonic acid in liquid and solid acid catalysts

Marziano

Ronchin

Tortato

et al. 2001

Journal of Molecular Catalysis A: Chemical

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“…siniple protonic acids, exceeded only by fluorosulfuric acid in this respect (1)(2)(3). Many of its derivatives, both organic and inorganic in nature, have been reported (1).…”

Section: Introductionmentioning

confidence: 99%

The synthesis and characterisation of the trifluoromethylsulfates of silver(II) and gold(III)

Leung¹,

Lee²,

Aubke³

1979

Can. J. Chem.

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“…Two main methods of synthesis of triflamides and other perfluoroalkanesulfonamides have been described: The reaction of the corresponding fluoroalkylsulfonyl fluorides RFSO 2 F with ammonia or amines, [1][2][3][4][5][6] and the raction of trifluoromethanesulfonyl chloride CF 3 SO 2 Cl or triflic anhydride (CF 3 SO 2 ) 2 O normally, in the presence of triethylamine to bind the eliminated triflic acid. [7][8][9] Different approaches based on the Mitsunobu reaction 10) and the intermolecular bromoesterification of allylic sulfonamides have also been reported. 11) However, the majority of these reactions have disadvantages such as: poor yield, multiple reaction steps, difficulty to workup, and the use of an excess of amine is required.…”

mentioning

confidence: 99%

An Efficient Strategy for the Synthesis of 1-(Trifluoromethylsulfonamido)propan-2-yl Esters and the Evaluation of Their Cytotoxic Activity

Gómez-García¹,

Gómez²,

Monzón-González³

et al. 2017

Chem. Pharm. Bull.

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An efficient method for the synthesis of 1-(trifluoromethylsulfonamido)propan-2-yl benzoates is described, the products of the reaction were characterized by heteronuclear single quantum coherence spectroscopy (HSQC), heteronuclear multiple bond correlation (HMBC) and NMR experiments. The overall process began with the activation of the oxazoline ring by triflic anhydride, followed by the opening of the five-membered ring in the 5-methyl-2-phenyl-4,5-dihydrooxazole system. The cytotoxic activity of the new trifluoromethyl sulfonamides was evaluated with six cancer cell lines and human gingival fibroblasts, posteriorly analyzing the influence on cytotoxicity exerted by the withdrawing and donor substituents at the para-position of the phenyl ring. Compounds 3b-e showed cytotoxic activity, with IC 50 values ranging from 17-17.44 µM for the cell lines tested, finding the highest effect for compound 3e.

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Trifluoromethanesulfonic acid and derivatives

Cited by 395 publications

References 62 publications

Acidity and reactivity of trifluoromethanesulfonic acid in liquid and solid acid catalysts

Acidity and reactivity of trifluoromethanesulfonic acid in liquid and solid acid catalysts

The synthesis and characterisation of the trifluoromethylsulfates of silver(II) and gold(III)

An Efficient Strategy for the Synthesis of 1-(Trifluoromethylsulfonamido)propan-2-yl Esters and the Evaluation of Their Cytotoxic Activity

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