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The reagent was used in trifluoromethylation of a thiophenolate. S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate is a commercially available and known trifluoromethylation reagent based on the same principle first documented in 1990. [64] [65] In this type of compound sulfur has been replaced by oxygen, selenium and tellurium.
Compared to methenium (the simplest carbenium ion), trifluoromethyl cation is more stable due to the presence of fluorine atoms.The fluorine atoms have lone pairs of electrons overlapping with the carbon atom.
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.
Complementarily, it can be produced by trifluoromethylation of 4-formylphenylboronic acid. [3] It readily condenses with amines to give imines. [4] It has been used in the synthesis of pharmaceuticals, such as Lanperisone. [5]
Trifluoromethyltrimethylsilane (known as Ruppert-Prakash reagent, TMSCF 3) is an organosilicon compound with the formula CF 3 Si(CH 3) 3.It is a colorless liquid. The compound is a reagent used in organic chemistry for the introduction of the trifluoromethyl group.
Togni reagent II is used for trifluoromethylation of organic compounds. For phenolates, the substitution takes place preferably in the ortho position. It is possible to obtain a second substitution by using an excess of Togni reagent II. [7] Reactions with alcohols yield the corresponding trifluoromethyl ethers. [8]
Fluoroform is weakly acidic with a pK a = 25–28 and quite inert. Attempted deprotonation results in defluorination to generate F − and difluorocarbene (CF 2).Some organocopper and organocadmium compounds have been developed as trifluoromethylation reagents.
More recently, trifluoromethylation of diazonium salts has been developed and is referred to as a 'Sandmeyer-type' reaction. Diazonium salts also react with boronates, iodide, thiols, water, hypophosphorous acid and others, [6] and fluorination can be carried out using tetrafluoroborate anions (Balz–Schiemann reaction). However, since these ...