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Trifluoromethanesulfonyl chloride (or triflyl chloride, CF3SO2Cl) can be used in a highly efficient method to introduce a trifluoromethyl group to aromatic and heteroaromatic systems, including known pharmaceuticals such as Lipitor. The chemistry is general and mild, and uses a photoredox catalyst and a light source at room temperature. [27]
Notably, triflidic acid is estimated to have an acidity 10 4 times that of triflic acid (pK a aq ~ –14), as measured by its acid dissociation constant. It was first prepared in 1987 by Seppelt and Turowsky by the following route: [2] (1) Tf 2 CH 2 + 2 CH 3 MgBr → Tf 2 C(MgBr) 2 + 2 CH 4 (2) Tf 2 C(MgBr) 2 + TfF → Tf 3 C(MgBr) + MgBrF
For example, n-butyl triflate can be written as CH 3 CH 2 CH 2 CH 2 OTf. The corresponding triflate anion , CF 3 SO − 3 , is an extremely stable polyatomic ion ; this comes from the fact that triflic acid ( CF 3 SO 3 H ) is a superacid ; i.e. it is more acidic than pure sulfuric acid , already one of the strongest acids known.
It is also used as an acidic titrant in nonaqueous acid-base titration because it behaves as a strong acid in many solvents (acetonitrile, acetic acid, etc.) where common mineral acids (such as HCl or H 2 SO 4) are only moderately strong. With a K a = 5 × 10 14, pK a = −14.7 ± 2.0, [1] triflic acid qualifies as a superacid. It owes many of ...
In organic chemistry, the triflyl group (systematic name: trifluoromethanesulfonyl group) is a functional group with the formula R−SO 2 CF 3 and structure R−S(=O) 2 −CF 3. The triflyl group is often represented by –Tf. The related triflate group (trifluoromethanesulfonate) has the formula R−OSO 2 CF 3, and is represented by –OTf. [1]
Trifluoromethyl group covalently bonded to an R group. The trifluoromethyl group is a functional group that has the formula-CF 3.The naming of is group is derived from the methyl group (which has the formula -CH 3), by replacing each hydrogen atom by a fluorine atom.
Triflic anhydride is prepared by dehydration of triflic acid using P 4 O 10. [2] Triflic anhydride is useful for converting ketones into enol triflates. [4] In a representative application, is used to convert an imine into a NTf group. [5] It will convert phenols into a triflic ester, which enables cleavage of the C-O bond. [6] [7]
CClF 2 CCl 2 F → C 2 F 3 Cl 2 + Cl• Cl• + O 3 → ClO• + O 2. This reaction is followed by: ClO• + O → Cl• + O 2. The process regenerates Cl• to destroy more O 3. The Cl• will destroy an average of 100,000 O 3 molecules during its atmospheric lifetime of 1–2 years. [12]