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Galstyan, A. G.; Tyupalo, N. F.; Andreev, P. Yu.

doi:10.1023/a:1022572701950

Cited by 3 publications

(4 citation statements)

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“…However, these hazardous and/or toxic oxidants generate copious amounts of wastes. Therefore, using a green oxidant such as molecular oxygen , or ozone − is gathering much attention according to the principle of green chemistry. It is well-known that molecular oxygen could hardly be activated in mild conditions.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient, Mild, Bromide-Free and Acetic Acid-Free Dioxygen Oxidation of p-Nitrotoluene to p-Nitrobenzoic Acid with Metal Phthalocyanine Catalysts

Song

She

et al. 2005

Org. Process Res. Dev.

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Four metal tetracarboxyl phthalocyanines were synthesized and characterized by elemental analysis and mass spectrometry. p-Nitrobenzoic acid was efficiently prepared in high yield from bromide-free and acetic acid-free aerobic oxidation of pnitrotoluene using metal phthalocyanines as catalysts under mild conditions in alkali-methanol solution. Up to 88.8% isolated yield of p-nitrobenzoic acid was obtained with the catalysis of tetracarboxyl phthalocyanine cobalt (0.13 mol %, based on the moles of p-nitrotoluene) optionally combined with a small amount of dimethylformamide in the presence of 2.0 MPa dioxygen at 30-60 °C. The effect on catalytic performance of a carboxyl group introduced into the phthalocyanine ring was further discussed on the basis of metal coordination chemistry theory.

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Section: Introductionmentioning

confidence: 99%

Highly Efficient, Mild, Bromide-Free and Acetic Acid-Free Dioxygen Oxidation of p-Nitrotoluene to p-Nitrobenzoic Acid with Metal Phthalocyanine Catalysts

Song

She

et al. 2005

Org. Process Res. Dev.

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“…In this case, no destructive oxidation of the aromatic system occurs since ozone reacts with the reduced form of the catalyst, Co(II)Br -. The reactive catalytic species Co(II)Br · is then reduced via oxidation of the methyl group in the substrate [7,8] (Scheme 4).…”

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confidence: 99%

Oxidation of 2-methylnaphthalene with ozone

Mamchur

Galstyan

2004

Russ J Org Chem

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In the oxidation of 2-methylnaphthalene with ozone in acetic acid, the oxidant reacts mainly at the double bonds of the substituted aromatic ring to give peroxy compounds. In the presence of cobalt diacetate and sodium bromide, oxidation of the 2-methyl group occurs with formation of 2-naphthoic acid. The major product in the oxidation of 2-methylnaphthalene with ozonated transition metal compounds is 2-methyl-1,4-naphthoquinone.

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“…We showed previously by an example of ozone reaction with 4-nitrotoluene that introduction of electronwithdrawing substituents into the para-position of the toluene aromatic ring decreased the aromatic system destruction by ozone: The fraction of products from the ozone reaction at the methyl group grew from 16.0% in toluenea to 24.2% in 4-nitrotoluene [1,2]. In extention of this study we investigated by an example of the ozone reaction with 2,4-dinitrotoluene the effect of the second nitro group attached to the ortho-OZONE REACTION WITH 2,4-DINITROTOLUENE IN ACETIC ACID SOLUTION position on the reaction direction and reaction products composition.…”

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confidence: 99%

“…At 323 K ozone reacts with dinitrotoluene (I) in the same way as with 4-nitrotoluene [2] along two competing pathways: at the methyl group (a) and at the aromatic ring (b) (see table and figure). The main products of the destructive oxidation of the aromatic ring are peroxide compounds XII, and the selective oxidation affords 2,4-dinitrobenzoic acid (X); the oxidation products accumulate concurrently.…”

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confidence: 99%