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Trimethylsilyl trifluoromethanesulfonate has a variety of other specialized uses. It has been used to install tert-alkyl groups on phosphine (R = alkyl): [6] PH 3 + R 3 C–OAc + Me 3 SiOTf → [(R 3 C) 2 PH 2]OTf. Deprotection of Boc-protected amines can be achieved using trimethylsilyl trifluoromethanesulfonate and triethylamine or 2,6 ...
tert-Butyldimethylsilyl chloride is an organosilicon compound with the formula (Me 3 C)Me 2 SiCl (Me = CH 3). It is commonly abbreviated as TBSCl or TBDMSCl. It is a chlorosilane containing two methyl groups and a tert-butyl group. As such it is more bulky that trimethylsilyl chloride. It is a colorless or white solid that is soluble in many ...
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 ...
The group is unaffected by treatment with 80% acetic acid, which catalyses the deprotection of O-tetrapyranyl, O-trityl and O-tert-butyldimethylsilyl ethers. It is also unaffected by 50% trifluoroacetic acid (TFA) , and survives the harsh acidic conditions used to install and remove isopropylidene or benzylidene acetals.
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 ...
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.
The acetate was removed by a tert-butyldimethylsilyl protecting group (ketone 6). Acetonide ethylene glycol, naphthalenesulfonic acid p-toluenesulfonic acid, acetone, and water. Ketone 3 (Scheme 1) was protected using an acetonide group, which was removed after the closure of ring D (ketone 14, Scheme 2). Bn (benzyl) benzyl chloride, pyridine
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).