Oxidation peracetic acid

Peracetic acid oxidation of l-methylquinoxalin-2-one (42) at 55°C gives l-methylquinoxaline-2,3-dione (43) in moderate yield, and similar treatment of l,3-dimethylquinoxalin-2-one (44) yields a small quantity of the 4-oxide, An improved yield of (43) is obtained by... 

Peracetic acid oxidation of 2,5-diphenyl-l,4-dithiadiene-l-oxide produces 2,5-diphenyl-l,4-dithiadiene-l, 1-dioxide in 72% yield without reaction with the sulphide sulphur atom40 (equation 13). This is rather surprising given the earlier evidence concerning relative rates37. 

The reaction mechanism for the peracid oxidation of thiosulphinates is perhaps more complex than described above. A study of the low-temperature ( — 40 °C) peracetic acid oxidation of 2-methyl-2-propyl 2-methyl-2-propanethiosulphinate gave two products as shown in equation (81)196. During the reaction the a-disulphoxide was apparently detected by NMR spectroscopy. 

M. Schnitzer and D. A. Hindle, Effect of peracetic acid oxidation on N-containing components of humic materials. Can. J. Soil Sci. 60 541 (1980). 

Ether solvents, such as THF, diethyl ether etc. are unsuitable solvents for peracetic acid oxidations, as interaction of the acid with the peroxidisable solvent is violent. 

Peracetic acid oxidation of l-benzyl-4-phenyltriazoles gives benzyloxy derivatives, possibly through an intermediate V-oxide. ... 

Cyclodehydration of 2-phenylthiocyclohexanone with a variety of reagents yielding 1,2,3,4-tetrahydrodibenzothiophene (64) as an oil has been reported,and represents the simplest way of obtaining this material (88%). Alternatively, reduction of 4-keto-1,2,3,4-tetrahydrodibenzothiophene under Huang-Minlon conditions affords 64 in high yield.Trace amounts of 64 were detected in the reduction of dibenzothiophene with calcium hexamine and during electrolysis in ethylenediamine-lithium chloride solution (Section III, C,4). Peracetic acid oxidizes 64 to its sulfone (65%), which... 

In a study of the chemistry of oxaziranes [75], it was discovered that this class of novel heterocyclic compounds is readily oxidized with peracetic acid to give dimeric nitroso compounds. Since the oxaziranes are, in turn, prepared by a peracetic acid oxidation of imines, the crude imines can, by proper adjust-... 

Instead of the peracetic acid oxidation just described, performic acid (prepared from 98 % formic acid and 90% hydrogen peroxide) may also be used as an oxidizing agent for the preparation of nitroso compounds. With this reagent, pentafluoronitrosobenzene and 4-nitrosotetrafluorobromobenzene have been prepared from the respective amines [85]. 

The oxidation of aromatic amines generally produces highly colored, tarry product mixtures. However, some aromatic amines have been successfully converted into azoxy compounds by peracetic acid oxidations. In regard to the factors influencing the reaction, several observations may be pertinent. 

Metal ions in catalytic amounts exercise a profound influence on the course of the oxidation. In the absence of metal ions, the peracetic acid oxidation of 3-nitroaniline produces 3,3 -dinitroazoxybenzene. In the presence of traces of cupric ions and, to a lesser extent, in the presence of small quantities of iron, nickel, and rhodium salts, only 3,3 -dinitroazobenzene is formed. The oxidation of toluidines and aminophenols usually leads to tarry products [32]. 

Of the various routes to diphenic acid, the present method and the peracetic acid oxidation of phenanthrene 7 seem to be the simplest. The yields are equally good. 

Pentamethylene dibromide, see 1 5-Dibromopentane Pentamethylene dicyanide, 493 2-Pentene, 239 4-Pentyn-l-ol, 896, 901 Peracetic acid oxidation, 755, 768, 893 Perbenzoic acid, 807, 808, 894 analysis of, 809 Performic acid, 893, 894 Periodic acid, 1070 reagent, 1070 ... 

Peracetic acid oxidation of 2-carbamoylquinoxaline (94) at 20°-25° gives the monoxides 95 and 96, and at higher temperatures the 1,4-dioxide (97) is isolated in 50% yield, together with a small amount of the 1,4-dioxide of 2-amino-3-quinoxalinone.m However, Hayashi and co-workers report the isolation of only 96 from 94 using monoperphthalic acid in ether <10°.109 In their attempt to correlate the nature of 2-substitution with the formation of 1- versus 4-oxides, they examined the behavior of some 2-alkyl substituted quinoxalines 113,114 2-ethylquin-oxaline gives the 1- and 4-oxides and the 1,4-dioxide, 2-isopropylquin-oxaline yields the 4-oxide and the 1,4-dioxide however, 2-f-butylquin-oxaline only furnishes the 4-oxide because of steric hindrance.114 The N-oxidation of 2-phenyl- and 2-alkyl-3-phenyl-quinoxalines with monoperphthalic acid furnishes the products shown in Table 1.114... 

Peracetic Acid Oxidation of 2-Butene Catalyzed by Bis (1-methyl-2-acetoxypropyl) selenide. Based upon the identification of an alkyl-selenenyl acetate among the products of the oxidation of bis(l-methyl-2-... 

This category includes several heterocyclic iodanes coming mainly from benziodazoles or benziodoxoles or a combination of both. Among them, 1-hydroxy-l,2-benziodazole and its derivatives are of considerable interest. It is noted that the first iodane of this type, prepared in 1965 by peracetic acid oxidation of o-iodobenzamide, is not N- (as originally proposed) but O-acetyl (Scheme 26) [77]. 

JV-benzoyl- and jV.V -dibenzoylethylenediamine, 2-phenylimidazo-line, and benzoic acid. The formation of these products is rationalized by mechanisms involving the initial addition of hydrogen peroxide to the dihydropyrazine to give the hydroperoxide. It appears therefore that the earlier report386 that peracetic acid oxidation of 5,6-diphenyl-2,3-dihydropyrazine gives the 1,4-di-iV-oxide is incorrect.386 ... 

Suitable control experiments had been carried out to establish that dibutyltin dichloride is not lost from the residue at 50 °C. and 12 mm. and to establish that the procedure for mercaptide removal (peracetic acid oxidation) did not interfere with the accuracy of the chloride analysis. 

Peracetic acid oxidizes l,6,6aA4-trithiapentalenes to l-oxa-6,6aA4-dithiapentalenes, most probably with intermediate formation of 5-oxides (71AHC(i3)16i,p. 180). 

Peracetic acid oxidizes 3-phenyl-5,6-dimethyl-1,2,4-triazine 4-oxide to the... 

Oxidation of ketones with non-peracetic acid oxidants. 

Parent and cross diperoxides are produced when tetra-sub-stituted olefins containing suitable substituents are ozonized. Cross diperoxides are also produced when pairs of tetra-substituted olefins are ozonized together. Comparison samples of diperoxides are conveniently synthesized by treating the appropriate ketone with peracetic acid at low temperature. Peracetic acid oxidation of ketone pairs can also be used to prepare cross diperoxides. Low temperature NMR is used to study diperoxide stereochemistry as well as barriers to conformational isomerization. 

Similar stereochemical possibilities are present when 11 is obtained from trans-l,3-dimethyl-3-hexene, 13, as a cross diperoxide from the ozon-olysis of 12 or from the peracetic acid oxidation of methyl ethyl ketone. 

---