Catalytic hydroperoxide oxidation of anthracene involving singlet oxygen

Гехман, А. Е.; Makarov, A. P.; Nekipelov, V. M.; Talzi, E. P.; Polotnyuk, O. Ya.; Zamaraev, K. I.; Моисеев, И. И.

doi:10.1007/bf00950175

Cited by 4 publications

(3 citation statements)

References 2 publications

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“…9,10-endoPeroxides are well-known intermediates in anthracene interactions with 1 O 2 and metalloperoxo complexes [26,34]. They are similar to 4, but there are no olefinic double bonds in their structures, so 3-type intermediates cannot be formed.…”

Section: Formation Of 14-naphthoquinone In Naphthalene Oxidation Catmentioning

confidence: 98%

“…We suppose that the peroxo complex ONPcMn(O 2 )(X) formed in the catalytic system ONPcMnCl AcOOH Nf may produce the wellknown 1,4-peroxy-1,4-dihydronaphthalene (intermediate 4, reaction 3, Scheme 2), interaction of which with the Mn oxene complex leads to 3 (reaction 4, Scheme 2). The insertion of two oxygen atoms at the 1, 4 positions of an aromatic molecule with intermediate endo-peroxide formation has been demonstrated in systems with vanadium (V) non-porphinoid complexes as catalysts of perfluorobenzene oxidation by perfluoroacetic acid [33] and anthracene oxidation by peracetic acid [34]. Thermal non-stability of 1,4-endoperoxides [23] may be the reason for 4 transformation to 1,4-dihydroxynaphthalene at 20°C followed by its oxidation to Q (reaction 5) [35].…”

Section: Formation Of 14-naphthoquinone In Naphthalene Oxidation Catmentioning

confidence: 98%

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Naphthalene Oxidation by Peracetic Acid Catalysed by Mn(III) Porphine-like Complexes: Nature of Intermediates and Pathways of their Formation

Barkanova

Kaliya

1999

J. Porphyrins Phthalocyanines

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Mn ( III ) complexes of meso-tetra(o,o′-dichlorophenyl)porphyrin, tetra-tert-butyl-tetraazaporphine and 3,5-octanitrophthalocyanine are efficient catalysts of naphthalene oxidation by peracetic acid in acetonitrile solution. The pathways of the reaction and the nature of intermediates and final products depend on the catalyst structure. For meso-tetra(o,o′-dichlorophenyl)porphyrin MnCl and tetra-tert-butyl-tetraazaporphine MnCl the single primary oxidation product is 1-naphthol. For 3,5-octanitrophthalocyanine MnCl, two pathways of naphthalene oxidation yielding 1-naphthol (as the primary product) and 1,4-naphthoquinone are proposed. The pathway of 1,4-naphthoquinone formation in the 3,5-octanitrophthalocyanine MnCl -catalysed reaction seems to involve two intermediates, 1,4-endo-peroxy-1,4-dihydro- and 2,3-epoxy-1,4-endo-peroxy-1,2,3,4-tetrahydronaphthalene.

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Section: Formation Of 14-naphthoquinone In Naphthalene Oxidation Catmentioning

confidence: 98%

Section: Formation Of 14-naphthoquinone In Naphthalene Oxidation Catmentioning

confidence: 98%

Naphthalene Oxidation by Peracetic Acid Catalysed by Mn(III) Porphine-like Complexes: Nature of Intermediates and Pathways of their Formation

Barkanova

Kaliya

1999

J. Porphyrins Phthalocyanines

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“…16 Even the first kinetic studies 16,17 have shown that the vanadium(V) complex responsible for the reactions involves at least three peroxo groups, that is, six oxygen atoms. Therefore, at the first stage of studies on the details of the mechanism of oxidative reactions, it seemed worthwhile to consider the structure and intra-sphere reactions of the [VO 6 ] -complex in the gas phase.…”

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confidence: 99%