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Trimethylsilyl trifluoromethanesulfonate (TMSOTf) is an organosilicon compound with the formula (CH 3) 3 SiO 3 SCF 3. It is a colorless moisture-sensitive liquid. It is the trifluoromethanesulfonate derivative of trimethylsilyl. [1] It is mainly used to activate ketones and aldehydes in organic synthesis.
Methyl trifluoromethanesulfonate, also commonly called methyl triflate and abbreviated MeOTf, is the organic compound with the formula CF 3 SO 2 OCH 3. It is a colourless liquid which finds use in organic chemistry as a powerful methylating agent. [2] The compound is closely related to methyl fluorosulfonate (FSO 2 OCH 3).
A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry.This group consists of three methyl groups bonded to a silicon atom [−Si(CH 3) 3], which is in turn bonded to the rest of a molecule.
In organic chemistry, triflate (systematic name: trifluoromethanesulfonate), is a functional group with the formula R−OSO 2 CF 3 and structure R−O−S(=O) 2 −CF 3. The triflate group is often represented by −OTf, as opposed to −Tf, which is the triflyl group, R−SO 2 CF 3. For example, n-butyl triflate can be written as CH 3 CH 2 CH ...
Trimethylsilyl trifluoromethanesulfonate (Me 3 SiOTf), normally considered a source of electrophilic silicon, has a 29 Si NMR shift of 43 ppm. [2] Salts of Si(C 6 H 2 Me 3) + 3 and Si(C 6 Me 5) + 3 have been crystallized with the carborane [HCB 11 Me 5 Br 6] − and decaborate [B 12 Cl 12] 2-, respectively.
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. Some common examples are trifluoromethane H– CF 3, 1,1,1-trifluoroethane H 3 C – CF 3, and hexafluoroacetone F 3 C –CO– CF 3. Compounds with this group are a subclass of the organofluorines.
TMSCl is reactive toward nucleophiles, resulting in the replacement of the chloride. In a characteristic reaction of TMSCl, the nucleophile is water, resulting in hydrolysis to give the hexamethyldisiloxane: + + The related reaction of trimethylsilyl chloride with alcohols can be exploited to produce anhydrous solutions of hydrochloric acid in alcohols, which find use in the mild synthesis of ...
Compared to the methyl radical the CF 3 radical is pyramidal (angle 107.8 °C ) with a large inversion barrier, electrophilic and also more reactive. In reaction with styrene it is 440 times more reactive. [52]