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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 ...
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]
It was also used in Takahashi Taxol total synthesis and in chemical glycosylation reactions. [5] 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
It is used to prepare alkyl triflates from alkyl halides: [5] CF 3 SO 2 OAg + RX → CF 3 SO 2 OR + AgX (X = iodide usually). In coordination chemistry, the salt is also useful to replace halide ligands with the more labile triflate ligand.
Lanthanide triflates are proposed for Friedel-Crafts acylations and alkylations, which are often carried out with AlCl 3 as the catalyst in an organic solvent. The nature of the Friedel-Craft reaction, especially the acylation, forces the AlCl 3 to irreversibly complex with any oxygen-containing group in the product, with the only way of decomplexing it being to destroy the AlCl 3 part with ...
Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is the chemical compound with the formula (CF 3 SO 2) 2 O. It is the acid anhydride derived from triflic acid. This compound is a strong electrophile, useful for introducing the triflyl group, CF 3 SO 2.
Copper(II) triflate is the copper(II) salt of trifluoromethanesulfonic acid (known simply as triflic acid) which has a chemical formula of Cu(OSO 2 CF 3) 2, abbreviated Cu(OTf) 2. This substance, first reported in 1972, [ 2 ] is a powerful Lewis acid .
Hf(OTf) 4, was the most effective in comparison to other Lewis acids including BF 3 • OEt 2, Sc(OTf) 3, and Zr(OTf) 4. Similalrly, Hf(OTf) 4 shows excellent activity in Friedel-Crafts alkylation’s, and enabled the alkylation of benzene with benzylic and tertiary alkyl chlorides.
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