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Dimethyl sulfone (DMSO 2) is an organosulfur compound with the formula (CH 3) 2 SO 2. It is also known by several other names including methyl sulfone and (especially in alternative medicine) methylsulfonylmethane (MSM). [4] This colorless solid features the sulfonyl functional group and is the simplest of the sulfones. It is relatively inert ...
Ms 2 O may be prepared by the dehydration of methanesulfonic acid with phosphorus pentoxide. [2] P 2 O 5 + 6 CH 3 SO 3 H → 3 (CH 3 SO 2) 2 O + 2 H 3 PO 4. Ms 2 O can be purified by distillation under vacuum (distillation of a solid) or by recrystallization from Methyl tert-butyl ether/toluene.
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]
Triflidic acid (IUPAC name: tris[(trifluoromethyl)sulfonyl]methane, abbreviated formula: Tf 3 CH) is an organic superacid. It is one of the strongest known carbon acids and is among the strongest Brønsted acids in general, with an acidity exceeded only by the carborane acids .
However, the use of dichloromethane is avoided since it can generate highly explosive azido-chloromethane and diazidomethane. The reaction may also instead be conducted in toluene, [3] acetonitrile, or pyridine. [4] Tf 2 O + NaN 3 → TfN 3 + NaOTf (Tf = CF 3 SO 2) An alternative route starts from imidazole-1-sulfonyl azide. [5]
The half-life is short in aqueous solutions (110 min at pH 7, 55 min at pH 7.5, and 35 min at pH 8, all at 25 °C). [2] At 4˚C, pH 8, PMSF is almost completely degraded after 1 day. [ 2 ] Stock solutions are usually made up in anhydrous ethanol , isopropanol , or corn oil and diluted immediately before use.
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.
NaDMSO condenses with esters (1) to form β-ketosulfoxides (2), which can be useful intermediates. [9] Reduction of β-ketosulfoxides with aluminium amalgam gives methyl ketones ( 3 ). [ 10 ] Reaction with alkyl halides followed by elimination gives α,β-unsaturated ketones ( 4 ). β-ketosulfoxides can also be used in the Pummerer ...