| 词条 | Trifluoromethanesulfonic anhydride |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 430483180 | ImageFile = Triflic-anhydride-2D.png | ImageName = Skeletal formula of triflic anhydride | ImageFileR1 = Trifluoromethanesulfonic anhydride Space Fill.png | ImageSizeR1 = 170px | ImageFileL1 = Trifluoromethanesulfonic anhydride Ball and Stick.png | ImageSizeL1 = 170px | IUPACName = |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 358-23-6 | PubChem = 67749 | ChemSpiderID = 61068 | SMILES = C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F | StdInChI = 1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8 | StdInChIKey = WJKHJLXJJJATHN-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=2 | F=6 | O=5 | S=2 | MeltingPt = | BoilingPtC = 82 [1] | Density = 1.6770 g/mL }} |Section7={{Chembox Hazards | ExternalSDS = [https://fscimage.fishersci.com/msds/45815.htm Fisher MSDS] | FlashPt = | RPhrases = {{R14}} {{R34}} | SPhrases = {{S25}} {{S26}} {{S36/37/39}} {{S45}} | RSPhrases = }} }}Triflic anhydride is the chemical compound with the formula (CF3SO2)2O. This compound is a particularly strong electrophile, useful for introducing the triflyl group, CF3SO2. Abbreviated Tf2O, triflic anhydride is the acid anhydride of the strong acid triflic acid, CF3SO2OH.[2] It can be assayed by 19F NMR spectroscopy: −72.6 ppm[3] vs. −77.3 for TfOH (std CFCl3). Illustrative usesIn a representative application, is used to convert an imine into a NTf group.[4] It will convert phenols into a triflic ester, which enables cleavage of the C-O bond.[5][6] See also
References1. ^{{cite journal|last1=Bloodworth|first1=A.J.|last2=Curtis|first2=Richard J.|last3=Spencer|first3=Michael D.|last4=Tallant|first4=Neil A.|title=Oxymetallation. Part 24. Preparation of cyclic peroxides by cycloperoxymercuriation of unsaturated hydroperoxides.|journal=Tetrahedron|date=March 1993|volume=49|issue=13|pages=2729–2750|doi=10.1016/S0040-4020(01)86350-X}} 2. ^{{cite journal|last1=Baraznenok|first1=Ivan L.|last2=Nenajdenko|first2=Valentine G.|last3=Balenkova|first3=Elizabeth S.|title=Chemical Transformations Induced by Triflic Anhydride|journal=Tetrahedron|date=May 2000|volume=56|issue=20|pages=3077–3119|doi=10.1016/S0040-4020(00)00093-4}} 3. ^{{cite journal|last=Dell'Amico|first=Daniela Belli|author2=Boschi, Daniele |author3=Calderazzo, Fausto |author4=Labella, Luca |author5= Marchetti, Fabio |title=Synthesis, and crystal and molecular structures of the triflato and trifluoroacetato complexes of zinc, Zn(O3SCF3)2(DME)2 and [Zn(O2CCF3)2(DME)]n|journal=Inorganica Chimica Acta|date=28 February 2002|volume=330|issue=1|pages=149–154|doi=10.1016/S0020-1693(01)00739-3|url=http://144.206.159.178/ft/458/52133/914984.pdf}} 4. ^{{OrgSynth |author1=Baker, T. J.|author2=Tomioka, M.|author3=Goodman, M. | title = Preparation and Use of N,N'-Di-BOC-N-Triflylguanidine | collvol = 10 | collvolpages 266 | year = 2004 | prep = v78p0091}} 5. ^{{OrgSynth |author1=McWilliams, J. C.|author2= Fleitz, F. J.|author3=Zheng, N.|author4=Armstrong, III, J. D. | title = Preparation of n-Butyl 4-Chlorophenyl Sulfide | collvol = 10 | collvolpages = 147 | prep = v79p0043}} 6. ^{{OrgSynth |author1=Cai, D.|author2=Payack, J. F.|author3=Bender, D. R.|author4=Hughes, D. L.|author5=Verhoeven, T. R.|author6=Reider, P. J. | title = (R)-(+)- and (S)-(−)-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl (BINAP) | collvol = 10 | collvolpages = 112 | prep = v76p0006}} 3 : Triflates|Acid anhydrides|Reagents for organic chemistry |
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