Organic Peroxides. XIX. α-Hydroperoxyethers and Related Peroxides

Milas, Nicholas A.; Peeler, R. L.; Mageli, Orville L.

doi:10.1021/ja01638a012

Cited by 65 publications

(30 citation statements)

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“…a-Hydroperoxytetrahydrofuran and 2-hydroperoxy-2,s-dimethyltetrahydrofuran were prepared by the a,a'-azo-bis-isobutyronitrile initiated oxidation at 30' of tetrahydrofuran and 2,s-dimethyltetrahydrofuran, respectively. a-Hydroperoxytetraliydropyran, a-ethoxyethyl hydroperoxide, and 2-hydroperoxy-2-nlethyltetrahydrofuran were prepared by the reaction of 50% H 2 0 2 with 2,3-dihydropyran, ethyl vinyl ether, and 2-methyl-4,s-dihydrofuran, respectively (10).…”

Section: Methodsmentioning

confidence: 99%

Absolute rate constants for hydrocarbon autoxidation. XVII. The oxidation of some cyclic ethers

Howard¹,

Ingold²

1969

Can. J. Chem.

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The propagation and termination rate constants have been determined for the autoxidation of 1,4-dioxan, tetrahydropyran, tetrahydrofuran, 2,s-dimethyltetrahydrofuran, and phthalan. The rate constants for a-hydrogen atom abstraction from sonle of the ethers by the tetralylperoxy radical and from tetralin by some ether peroxy radicals have been measured and compared. The chain transfer rate constants have been estimated for the reaction of the c~~mylperoxy radical with a-hydroperoxytetrahydrofuran, a-hydroperoxytetrahydropyran, and a-ethoxyethyl hydroperoxide.

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Section: Methodsmentioning

confidence: 99%

Absolute rate constants for hydrocarbon autoxidation. XVII. The oxidation of some cyclic ethers

Howard¹,

Ingold²

1969

Can. J. Chem.

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“…The reaction of furan with hydrogen peroxide in the presence of sulfuric acid was studied in [29,30]. It was suggested that this reaction leads to the formation of the unstable intermediate hydroperoxide 31, which is converted by the action of hydrogen peroxide into the hydroxydihydroperoxide 32.…”

Section: Oxidation Of Furans By Hydrogen Peroxidementioning

confidence: 99%

“…The latter in turn changes into the hydroxyhydroperoxide 33, which rearranges to the more stable ozonide 34. This ozonide was isolated in the individual form by the authors of [29,30]. During catalytic hydrogenation compound 34 is converted into the malonaldehyde 2 (scheme 10), isolated in the form of the 2,4-dinitrophenylhydrazone [29,30].…”

Section: Oxidation Of Furans By Hydrogen Peroxidementioning

confidence: 99%

“…This ozonide was isolated in the individual form by the authors of [29,30]. During catalytic hydrogenation compound 34 is converted into the malonaldehyde 2 (scheme 10), isolated in the form of the 2,4-dinitrophenylhydrazone [29,30]. It was established [29,30] that 2-methylfuran is oxidized to the corresponding keto aldehyde under these conditions.…”

Section: Oxidation Of Furans By Hydrogen Peroxidementioning

confidence: 99%

“…During catalytic hydrogenation compound 34 is converted into the malonaldehyde 2 (scheme 10), isolated in the form of the 2,4-dinitrophenylhydrazone [29,30]. It was established [29,30] that 2-methylfuran is oxidized to the corresponding keto aldehyde under these conditions. The oxidation of furan by hydrogen peroxide in the gas phase at 160-170°C was investigated in [31].…”

Section: Oxidation Of Furans By Hydrogen Peroxidementioning

confidence: 99%

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Oxidation of furans (Review)

Badovskaya

Поварова

2009

Chem Heterocycl Comp

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Published data and the results of the authors' own investigations on the catalytic oxidation of furan and its homologs under various conditions are reviewed. The mechanisms and the characteristics and composition of the products from the transformations of furans are discussed in relation to the type of oxidizing agent and the reaction conditions. The prospects of using the oxidation processes of furan and its homologs in the synthesis of alkoxy-and dialkoxydihydrofurans, 5-alkoxy-2(5H)-furanones, β-formylacrylic acid, maleic acid, and its dialdehyde are indicated.The oxidation reactions of furans have attracted the attention of researchers over many years. The expediency of a comprehensive study of oxidation processes in furan and its homologs arises from the possibility of obtaining a whole series of prospective compounds for fine organic synthesis and the chemistry of biologically active substances on the basis of these processes. Molecular oxygen or peroxides (peracids and hydrogen peroxide) have been used as oxidizing agents in certain oxidation reactions of furans. Oxidation of Furan and its Homologs with Molecular OxygenThe results of investigations of the processes involved in the vapor-phase oxidation of furans with molecular oxygen are presented in [1][2][3][4][5][6][7][8]. In the opinion of the authors in [1] the oxidation of furan in the presence of vanadium(V) oxide takes place through a stage involving the formation of the endoperoxide 1, structurally related to ozonides, and malealdehyde (2). This is then oxidized to maleic acid (3), which is isolated as the main product [1] (Scheme 1).

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