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In these cases, triflic acid is a typical proton donor.
Triflic acid is mainly used in research as a catalyst for esterification.
The excess oxide ensures all of the triflic acid is consumed.
Addition of triflic acid to polar solvents can be dangerously exothermic.
Initiators are strong electrophiles such as triflic acid.
Triflic acid is a 'superacid' so its conjugate base ions are very stable.
The triflate-group (the conjugate base of the triflic acid) is a good leaving group in substitution reactions.
They can be obtained directly from triflic acid and the metal hydroxide or metal carbonate in water.
Triflic acid reacts exothermically with alcohols to produce ethers and olefins.
Allyldimethylsilyl triflate 2 may be prepared by a protiodesilylation reaction between diallyldimethylsilane and triflic acid.
For preparative purposes triflic acid is recommended:
Triflic acid is purified by distillation from triflic anhydride.
Common acids used are phosphoric, sulfuric, fluro-, and triflic acids.
Lanthanide triflates are synthesized from lanthanide oxide and aqueous triflic acid.
Attempts to make the corresponding triflate were unsuccessful because traces of free triflic acid cleaved the Au-C bonds.
The polymeric analogue of triflic acid, nafion is a solid acid that is used as the membrane in most low temperature fuel cells.
Triflic acid promotes other Friedel-Crafts-like reactions including the cracking of alkanes and alkylation of alkenes, which are very important to the petroleum industry.
When triflic acid concentration was increased these products were avoided but acid-catalyzed migration of a 2-O-acetyl group led to both 1→2 and 1→3 linked trisaccharides 35 and 37.
Triflic acid reacts with acyl halides to give mixed triflate anhydrides, which are strong acylating agents, e.g. in Friedel-Crafts reactions.
Trifluoromethanesulfonic acid (or triflic acid, CFSOH)
TMTHF reacts with benzene in the presence of triflic acid to form 1,1,4,4-dimethyl tetralin and symmetric tetramethyl octahydroanthracene.
The dimer however is part of series of equilibria between polyacetal macrocycles of different size brought about by acid catalyzed (triflic acid) transacetalization.
The ionic hydrogenation of diarylcarbinols by triethylsilane, in the presence of catalytic amount of triflic acid proceeds via dibenzhydryl ethers.
Further recommending its use, triflic acid does not sulfonate substrates, which can be a problem with sulfuric acid, fluorosulfuric acid, and chlorosulfonic acid.
These triflic acid derivative catalysts are very effective in isomerizing straight chain or slightly branched hydrocarbons that can increase the octane rating of a particular petroleum-based fuel.
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