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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 ...
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 ...
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.
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]
In the CF 3 radical the fluorine atom is an electron-withdrawing group via the inductive effect but also a weak pi donor through interaction of the fluorine lone pair with the radical center's SOMO. Compared to the methyl radical the CF 3 radical is pyramidal (angle 107.8 °C ) with a large inversion barrier, electrophilic and also more
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.