Trifluoromethanesulfonic anhydride

From Wikipedia, the free encyclopedia
  (Redirected from Triflic anhydride)
Jump to: navigation, search
Trifluoromethanesulfonic anhydride
Skeletal formula of triflic anhydride
Identifiers
CAS number 358-23-6 YesY
Properties
Molecular formula C2F6O5S2
Molar mass 282.14 g mol−1
Density 1.6770 g/mL
Boiling point 82 °C (180 °F; 355 K)
Hazards
MSDS Fisher MSDS
R-phrases R14 R34
S-phrases S25 S26 S36/37/39 S45
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

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. Triflic anhydride is the acid anhydride of the strong acid triflic acid, CF3SO2OH.[1]

It can be assayed by 19F NMR spectroscopy: −72.6 ppm[2] vs. -77.3 for TfOH (std CFCl3).


Illustrative uses[edit]

In a representative application, is used to convert an imine into a NTf group.[3]

It will convert phenols into a triflic ester, which enables cleavage of the C-O bond.[4][5]

References[edit]

  1. ^ Chemical Transformations Induced by Triflic Anhydride, Tetrahedron 56 (2000) 3077-3119,Baraznenok
  2. ^ Dell'Amico, Daniela Belli; Boschi, Daniele; Calderazzo, Fausto; Labella, Luca; Marchetti, Fabio (28 February 2002). "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". Inorganica Chimica Acta 330 (1): 149–154. doi:10.1016/S0020-1693(01)00739-3. 
  3. ^ Baker, T. J. Tomioka, M.; Goodman, M. (2004), "Preparation and Use of N,N'-Di-BOC-N-Triflylguanidine", Org. Synth. ; Coll. Vol. 10 
  4. ^ McWilliams, J. C. Fleitz, F. J.; Zheng, N.; Armstrong, III, J. D., "Preparation of n-Butyl 4-Chlorophenyl Sulfide", Org. Synth. ; Coll. Vol. 10: 147 
  5. ^ Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J., "(R)-(+)- and (S)-(−)-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl (BINAP)", Org. Synth. ; Coll. Vol. 10: 112