Trifluoromethanesulfonic anhydride
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Trifluoromethanesulfonic anhydride | |||||||||||||||
Molecular formula | C 2 F 6 O 5 S 2 | |||||||||||||||
Brief description |
colorless liquid |
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properties | ||||||||||||||||
Molar mass | 282.139 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
1.677 g cm −3 |
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boiling point |
82 ° C |
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solubility |
good in organic solvents |
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Refractive index |
1.321 |
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safety instructions | ||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
Trifluoromethanesulfonic anhydride , abbreviated as Tf 2 O, is a colorless, corrosive and toxic liquid that is readily soluble in organic solvents, but reacts violently with protic solvents with hydrolysis . It is the anhydride of trifluoromethanesulfonic acid . The compound is a particularly strong electrophile , it is used to introduce the triflyl group . An overview of various reactions is given in the literature.
Presentation and extraction
Trifluoromethanesulfonic anhydride can be obtained by condensation from trifluoromethanesulfonic acid using phosphorus pentoxide or phosphorus pentachloride .
use
In preparative organic chemistry, the triflyl group introduced by trifluoromethanesulfonic anhydride is used as a good leaving group . With alcohols , alkyl triflates result, which are used, among other things, for alkylations. Vinyl and aryl triflates are formed from carbonyl compounds and phenols , which are a superior alternative to halides in the Heck reaction or other cross-couplings . It also serves as a good leaving group in aminations, carbonylations, or heterocyclizations.
Individual evidence
- ↑ a b c Entry on trifluoromethanesulfonic anhydride. In: Römpp Online . Georg Thieme Verlag, accessed on June 23, 2020.
- ↑ a b c d data sheet Trifluoromethanesulfonic anhydride from Sigma-Aldrich , accessed on January 9, 2015 ( PDF ).
- ^ AJ Bloodworth, Richard J. Curtis, Michael D. Spencer, Neil A. Tallant: Oxymetallation. Part 24. Preparation of cyclic peroxides by cycloperoxymercuriation of unsaturated hydroperoxides. . In: Tetrahedron . 49, No. 13, March 1993, pp. 2729-2750. doi : 10.1016 / S0040-4020 (01) 86350-X .
- ↑ Ivan L. Baraznenok, Valentine G. Nenajdenko, Elizabeth S. Balenkova: Chemical Transformations Induced by Triflic Anhydride . In: Tetrahedron . 56, No. 20, May 2000, pp. 3077-3119. doi : 10.1016 / S0040-4020 (00) 00093-4 .
- ^ André B. Charette, Peter Chua: A new method for the conversion of secondary and tertiary amides to bridged orthoesters . In: Tetrahedron Letters . 38, No. 49, December 1997, pp. 8499-8502. doi : 10.1016 / S0040-4039 (97) 10310-0 .
- ↑ e-EROS Encyclopedia of Reagents for Organic Synthesis , 1999-2013, John Wiley and Sons, Inc., entry for Trifluoromethanesulfonic Anhydride, accessed January 6, 2015 .
- ↑ Kurt Ritter: Synthetic Transformations of Vinyl and Aryl Triflates . In: Synthesis . 1993, No. 08, 1993, pp. 735-762. doi : 10.1055 / s-1993-25931 .
- ↑ Farina Vittorio, Krishnamurthy Venkat, Scott J. William: The Stille Reaction . In: Organic Reactions . September. doi : 10.1002 / 0471264180.or050.01 .
- ↑ Rik R. Tykwinski, Yuming Zhao: Cross-Conjugated oligo (enynes) . In: Synlett . No. 12, 2002, pp. 1939-1953. doi : 10.1055 / s-2002-35578 .
- ↑ John F. Hartwig: Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism . In: Angewandte Chemie International Edition . 37, No. 15, August 17, 1998, pp. 2046-2067. doi : 10.1002 / (SICI) 1521-3773 (19980817) 37:15 <2046 :: AID-ANIE2046> 3.0.CO; 2-L .
- ↑ Sandro Cacchi, Giancarlo Fabrizi, Luca M. Parisi: Nitrogen-containing Heterocycles via Palladium-catalyzed Reaction of Alkynes with Organic Halides or Triflates . In: HETEROCYCLES . 58, No. 1, 2002, p. 667. doi : 10.3987 / REV-02-SR (M) 1 .
- ↑ Ernesto Occhiato: Lactam-derived Vinyl Triflates and Phosphates in the Synthesis of N-heterocycles . In: Mini-Reviews in Organic Chemistry . 1, No. 2, April 1, 2004, pp. 149-162. doi : 10.2174 / 1570193043488890 .