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The first to investigate trifluoromethyl groups in relationship to biological activity was F. Lehmann in 1927. [5] An early review appeared in 1958. [6] An early synthetic method was developed by Frédéric Swarts in 1892, [7] based on antimony fluoride.
Trifluoromethyl group covalently bonded to an R group. The trifluoromethyl group is a functional group that has the formula-CF 3. 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 ...
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]
Unlike the phenyl sulfones, this alkoxide intermediate (2) is more reactive and will undergo a Smiles rearrangement to give the sulfinate salt (4). The sulfinate salt (4) will spontaneously eliminate sulfur dioxide and lithium benzothiazolone (5) producing the desired alkene (6). The mechanism of the benzothiazole variation of the Julia olefination
Two other isomers are also known: 2-trifluoromethylbenzaldehyde and 3-trifluoromethylbenzaldehyde. These compounds are derivatives of benzaldehyde with trifluoromethyl substituents. The CF 3 group enhances the electrophilicity of the formyl group and provides a label for analysis by fluorine-19 nuclear magnetic resonance spectroscopy .
The compound is closely related to methyl fluorosulfonate (FSO 2 OCH 3). Although there has yet to be a reported human fatality, several cases were reported for methyl fluorosulfonate (LC 50 (rat, 1 h) = 5 ppm), and methyl triflate is expected to have similar toxicity based on available evidence.
[1] Its p K a value in water cannot be accurately determined but in acetonitrile it has been estimated as −0.10 and in 1,2-dichloroethane −12.3 (relative to the p K a value of 2,4,6-trinitrophenol ( picric acid ), anchored to zero to crudely approximate the aqueous p K a scale [ 2 ] ), making it more acidic than triflic acid (p K a MeCN = 0 ...
Trifluoromethanesulfonyl azide is prepared by treating trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane. [1] However, the use of dichloromethane is avoided since it can generate highly explosive azido-chloromethane and diazidomethane.
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