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Versatile application of trifluoromethyl triflate |
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| Authors: | Alexander A. Kolomeitsev Mikhail Vorobyev |
| Affiliation: | a Institute of Inorganic and Physical Chemistry, University of Bremen, Leobener Strasse, 28334 Bremen, Germany b Hansa Fine Chemicals GmbH, Fahrenheitstr. 1, 28359 Bremen, Germany c SciChem GmbH, Fahrenheitstr. 1, 28359 Bremen, Germany |
| Abstract: | Hydrolytically stable and easy to handle trifluoromethyl triflate was found to be a liquid reservoir of ‘masked’ difluorophosgene. Anhydrous F− sources cleave the S-O bond in trifluoromethyl triflate yielding quantitatively the trifluoromethanolate salts, being useful trifluoromethoxy group carriers. Reaction of trifluoromethanolates with in situ generated from o-trimethylsilylphenyl triflate benzyne leads to (trifluoromethoxy)benzene and fluorobenzene (ratio 85:15). Whereas an addition of trifluoromethanethiolate anion across a triple bond of benzyne leads to [(trifluoromethyl)sulfanyl]benzene solely. |
| Keywords: | Trifluoromethyl triflate Trifluoromethanolates Trifluoromethyl ethers Arynes Delocalized lipophilic cations |
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