Peroxytrifluoroacetic acid

PEROXIDES AND PEROXIDE COMPOUNDS - ORGANIC PEROXIDES] (Vol 18) Peroxytrifluoroacetic acid [359-48-8]... 

Nitroso compounds are formed selectively via the oxidation of a primary aromatic amine with Caro s acid [7722-86-3] (H2SO ) or Oxone (Du Pont trademark) monopersulfate compound (2KHSO KHSO K SO aniline black [13007-86-8] is obtained if the oxidation is carried out with salts of persulfiiric acid (31). Oxidation of aromatic amines to nitro compounds can be carried out with peroxytrifluoroacetic acid (32). Hydrogen peroxide with acetonitrile converts aniline in a methanol solution to azoxybenzene [495-48-7] (33), perborate in glacial acetic acid yields azobenzene [103-33-3] (34). 

A variety of esters can be prepared from the corresponding ketones usiag peracids ia a process usually referred to as the Baeyer-Villiger reaction (95) ie, cyclopentanone is converted to 5-valerolactone upon treatment of the ketone with peroxytrifluoroacetic acid ... 

A very common oxidizing reagent is peroxytrifluoroacetic acid, which is usually generated in situ from trifluoroacetic acid [29, 30, 31] or trifluoroacetic anhydride [32, 33, 34] and hydrogen peroxide Peroxytrifluoroacetic acid is one of the most efficient epoxidizing reagents [35] It can be used to prepare epoxides... 

As peracids are used peracetic acid, peroxytrifluoroacetic acid, m-chloroperben-zoic acid and others. Hydrogen peroxide or a peracid in combination with triflu-oroacetic acid or certain organoselenium compounds have been successfully employed. 

Chloro-l-aryl-3//-2-benzazepine /V-oxides, with the exception of the 1,4,5-triaryl derivative 1 which yields the epoxide 2,178 undergo no further oxidation with 3-chioroperoxybenzoic acid (see Section 3.2.1.5.1. ). 8 However, oxidations of l-aryi-3ff-2-benzazepines as their meth-anesulfonates, e.g. 3, with peroxytrifluoroacetic acid produce mixtures of the epoxides, e.g. 4, and the Af-oxides, e.g. 5.78... 

N-Nitromorpholine has been prepared by the oxidation of N-nitrosomorpholine with peroxytrifluoroacetic acid,4 by the... 

Anhydrous peroxytrifluoroacetic acid is not easy to handle, but the procedure has recently been revised.121 Namely, reaction of urea-hydrogen peroxide complex (UHP) with tri-fluoroacetic anhydride in acetonitrile at 0 °C gives solutions of peroxytrifluoroacetic acid, which oxidize aldoximes to nitroalkanes in good yields (Eqs. 2.58 and 2.59). Ketoximes fail to react under these conditions, the parent ketone being recovered. 

FIGURE 15.25 IR spectra of SWNTs (a) p-SWNTs, (b) after peroxytrifluoroacetic acid treatment, and (c) N2 annealing after treatment. (Reprinted with permission from [158], Copyright (2005) Elsevier.)... 

M. Liu, Y. Yang, T. Zhu, and Z. Liu, Chemical modification of single-walled carbon nanotubes with peroxytrifluoroacetic acid. Carbon 43, 1470-1478 (2005). 

Mesitylene, condensation with dichioro-methyl methyl ether, 47, 1 oxidation with peroxytrifluoroacetic acid and boron trifluoridc, 48, 90... 

Peroxytrifluoroacetic acid, in oxidation, of hexamethyl benzene, 48, 87 of polyalkylarenes, 48, 89, 90 Peroxyvanadic acid, 45, 27 Phenanthrene, 9-phenyl-, 46, 91... 

Caution The preparation and handling of peroxytrifluoroacetic acid should be carried out behind a safety screen. Precautions to be observed with 90% hydrogen peroxide are described in Note 3 and should be followed carefully. 

A solution of 24.2 g. (0.15 mole) of hexamethylbenzene in 300 ml. of distilled methylene chloride is prepared in a 1-1. threenecked flask equipped with two ice-jacketed addition funnels (Note 5) and a thermometer. The solution is cooled to 5° in an ice-ethanol bath and is agitated by a magnetic stirrer. The cold peroxytrifluoroacetic acid solution is added at a constant rate to the hexamethylbenzene solution from one of the ice-jacketed... 

Boron trifluoride gas may be used in place of the etherate. In this case a fritted-glass gas-dispersion tube that extends below the liquid surface replaces the second addition funnel. Boron trifluoride gas (0.20 mole, 4.48 1.) is passed through the solution as the peroxytrifluoroacetic acid is added. The boron trifluoride may be metered into the mixture through a calibrated flowmeter containing carbon tetrachloride as the indicator liquid. Alternatively, a premeasured quantity of boron trifluoride may be displaced by carbon tetrachloride from a gas bulb. The yield is approximately the same regardless of the source of boron trifluoride. 

These relations are called Baeyer-Villiger rearrangement and in such reactions peroxytrifluoroacetic acid is used as an oxidising agent. 

Palladium(II) oxide, 4825 Palladium(IV) oxide, 4835 Perchloric acid, 3998 Periodic acid, 4425 Permanganic acid, 4434 Peroxodisulfuric acid, 4482 Peroxodisulfuryl difluoride, 4328 Peroxomonosulfuric acid, 4481 Peroxytrifluoroacetic acid, 0666 Platinum hexafluoride, 4371 Platinum(IV) oxide, 4836 Plutonium hexafluoride, 4372 Potassium bromate, 0255 Potassium chlorate, 4017 Potassium dichromate, 4248 Potassium iodate, 4619 Potassium nitrate, 4650 Potassium nitrite, 4649 Potassium perchlorate, 4018 Potassium periodate, 4620 Potassium permanganate, 4647 Rhenium hexafluoride, 4373 Rubidium fluoroxysulfate, 4309 Ruthenium(VIII) oxide, 4862 Selenium dioxide, 4838 Selenium dioxide, 4838 Silver permanganate, 0021 Sodium chlorate, 4039 Sodium chlorite, 4038 Sodium dichromate, 4250 Sodium iodate, 4624 Sodium nitrate, 4721 Sodium nitrite, 4720... 

Benzeneperoxyseleninic acid, 2337 Benzeneperoxy sulfonic acid, 2341 3-Chloroperoxybenzoic acid, 2676 Diperoxyazelaic acid, 3189 Diperoxyterephthalic acid, 2925 Monoperoxysuccinic acid, 1542 Peroxyacetic acid, 0837 Peroxybenzoic acid, 2733 3-Peroxycamphoric acid, 3348 Peroxycrotonic acid, 1535 Peroxyformic acid, 0420 Peroxyfuroic acid, 1837 Peroxyhexanoic acid, 2514 Peroxy propionic acid, 1236 Peroxytrifluoroacetic acid, 0666 Trichloroperoxyacetic acid, 0659 See 1 /-DI(BENZOYLPEROX Y)ARYLIODINES POLYMERIC PEROXYACIDS ORGANIC PEROXIDES... 

Oxidation, of hexamethylbenzene with peroxytrifluoroacetic acid and boron trifluoride, 48, 87 of imines by perbenzoic acid, 49, 13 of 18-iodo- and 18-hydroxy-18,20-oxidosteroid to 18,20-lactone, 4B, 57... 

Dichloronitrobenzene has been prepared by deamination of 3,5-dichloro-4-nitroaniline and of 2,4-dichloro-3-nitroaniline. This procedure is an example of the rather general oxidation of anilines to nitrobenzenes with peroxytrifluoroacetic acid. Use of this reagent is frequently the method of choice for carrying out this transformation, and it is particularly suitable for oxidation of negatively substituted aromatic amines. Conversely, those aromatic amines, such as />-anisidine and j8-naphthylamine, whose aromatic nuclei are unusually sensitive to electrophilic attack give intractable mixtures with this reagent. This is not... 

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