Étude quantitative des réactions d'ozonolyse. IV. Ozonation de l'indène

Fliszár, Sándor; Bełżecki, C.; Chylińska, J. B.

doi:10.1139/v67-043

Cited by 14 publications

(14 citation statements)

References 5 publications

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“…Ozonolyses of a number of unsaturated cyclic compounds in methanol have been reported to give cyclic hemiperacetals (1)(2)(3)(4). In line with this, we found that ozonolysis of l-methylcyclopentene in methanol gave l a , 8a, and l l a in a molar ratio of 90:8:2 (5).…”

Section: Introductionsupporting

confidence: 87%

Acid-catalyzed reactions of six- and seven-membered cyclic hemiperacetals and peracetals and of related bicyclic ozonides

Griesbaum¹,

Kiesel²,

Mertens³

et al. 1994

Can. J. Chem.

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. Can. J. Chem. 72,2 198 (1994). HC1-catalyzed reactions of the hemiperacetals 3-methoxy-3-methyl-7-hydroxy-1,2-dioxepane (la) and 3-methoxy-3-methyl-6-hydroxy-1,2-dioxane (lb) and of the related ozonides 1-methyl-6,7,8-trioxabicyclo[3.2. lloctane (20) and 1-methyl-5,6,7-trioxabicyclo[2.2.l]heptane (2b) gave peroxidic monocyclic (11-13), bicyclic (14), and (or) tricyclic (15) products. By contrast, reactions of the peracetals corresponding to l a and lb, viz., 3-methyl-3,7-dimethoxy-1,2-dioxepane (13a) and 3-methyl-3,6-dimethoxy-l,2-dioxane (13b) gave only non-peroxidic products. Reactions of the persubstituted peracetals 3,6-dimethoxy-3,6-dimethyl-l,2-dioxane (25) and 3,6-dimethoxy-3-isopropyl-6-methyl-l,2-dioxane (27) also gave non-peroxidic products, which resulted from fragmentation of the carbon skeletons.KARL GRIESBAUM, GILBERT KIESEL, HEW MERTENS, PETRA KRIU;ER-BECK et HENNING HENKE. Can. J. Chem. 72,2 198 (1994). Les reactions catalystes par le HC1 des hkmiperacetals 3-mkthoxy-3-mkthyl-7-hydroxy-1,2-dioxepane (la) et 3-mtthoxy-3-mtthyl-6-hydroxy-l,2-dioxane (lb) et des ozonides apparentts 1-mtthyl-6,7,8-trioxabicyclo[3.2.l]octane (2a] et l-mkthyl-5,6,7-trioxabicyclo[2.2. Ilheptane (2b) conduisent respectivement aux produits peroxydks monocycliques (11-13) et bicyclique (14) et (ou) tricyclique (15). Par opposition, les rkactions des peracetals correspondants i l a et lb, les 3-methyl-3,7-dimethoxy-1,2-dioxepane (l3a) et 3-methyl-3,6-dimethoxy-1,2-dioxane (13b) ne donnent que des produits non peroxydts. Les reactions des peracetals persubstituks 3,6-dimethoxy-3,6-dimkthyl-1,2-dioxane (25) et 3,6-dim~thoxy-3-isopropyl-6-m~thyl-l,2-dioxane (27) fournissent aussi des produits non peroxydks qui rksultent de la fragmentation des squelettes carbonks.[Traduit par la rkdaction]

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Section: Introductionsupporting

confidence: 87%

Acid-catalyzed reactions of six- and seven-membered cyclic hemiperacetals and peracetals and of related bicyclic ozonides

Griesbaum¹,

Kiesel²,

Mertens³

et al. 1994

Can. J. Chem.

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“…It was reported that the largest negative charge in the ground state is located on the oxygen atom of the carbonyl group present in the coniferyl aldehyde molecule. [33] When the particles coated with coniferyl aldehyde are illuminated by simulated sunlight, the negative charge on the oxygen atom of the C=O group further increases when the molecule is excited from the ground state to the triplet state. The latter implies a raise of the nucleophilic properties of the molecule which is most likely responsible for the high reactivity of carbonyl compounds in their excited triplet states.…”

Section: First-order Rate Constantsmentioning

confidence: 99%

“…[51][52] Fliszar et al exhibited that in cases where an organic compound contains both an aromatic ring and a C=C alkene bond the ozone attacks preferentially the C=C bond. [33] Coniferyl aldehyde contains both an aromatic ring and an unsaturated alkene C=C bond. Therefore, we suggest that the reaction of gas-phase ozone with coniferyl aldehyde proceeds via a concerted cycloaddition process which implies a bridging addition of ozone to the C=C bond as depicted in Scheme 1.…”

Section: Ozonolysis Mechanismmentioning

confidence: 99%

“…The reaction mechanism of gas-phase ozone with organic compounds containing C=C bonds is complex, and for many years it has been a focus of interest. [31][32][33][34][35] Ozone is known to react with aromatic compounds leading either to a substitution (atom attack) or to a ring opening (bond attack). The location of ozone attack can be correlated with the lowest atom or bond localisation energies of the target compound.…”

Section: Ozonolysis Mechanismmentioning

confidence: 99%

“…The CI is a carbonyl oxide which can exist in the syn-or anti-configuration. [33,[53][54] Scheme 1 shows that after rearrangement of the atoms, CI 1 yields glycolic acid and glyoxylic acid.…”

Section: Ozonolysis Mechanismmentioning

confidence: 99%

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Photolysis and Heterogeneous Reaction of Coniferyl Aldehyde Adsorbed on Silica Particles with Ozone

et al. 2010

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The pseudo-first-order loss of coniferyl aldehyde, adsorbed on silicon dioxide particles, upon heterogeneous ozonolysis was monitored at various ozone mixing ratios in the absence and presence of simulated sunlight. For the first time we investigated the effect of light on the heterogeneous ozonolysis of coniferyl aldehyde adsorbed on silica particles. We found that UV-VIS light (λ>300 nm) does not impact the degradation of coniferyl aldehyde by ozone but induces an additional, slow photolysis of the aldehyde with a photolytic rate constant of ~10(-5) s(-1). In both cases, that is, in presence and/or absence of light, the heterogeneous ozonation kinetics are well described by an immediate gas-surface reaction formalism with light-independent rate constants of k(2nd)=(7.2±0.9)×10(-19) cm(3) molec(-1) s(-1) and (7.6±1.7)×10(-19) cm(3) molec(-1) s(-1) in the absence and presence of light, respectively. Five oxidation products: glycolic acid, oxalic acid, vanillin, vanillic acid and 3,4-dihydroxybenzoic acid were identified and confirmed by their corresponding standards. Vanillin and vanillic acid absorb light in the region λ>300 nm and thus can further participate in the direct and indirect photolysis processes of atmospheric relevance. A reaction mechanism is proposed in order to elucidate the ozonolysis reaction and to explain the reaction products.

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Ozonolysen von 1‐Methylcyclopenten, 1‐Methylcyclobuten, 5‐Hexen‐2‐on und Naturkautschuk im Beisein von Methanol

Griesbaum

Kiesel

1989

Chem. Ber.

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Étude quantitative des réactions d'ozonolyse. IV. Ozonation de l'indène

Cited by 14 publications

References 5 publications

Acid-catalyzed reactions of six- and seven-membered cyclic hemiperacetals and peracetals and of related bicyclic ozonides

Acid-catalyzed reactions of six- and seven-membered cyclic hemiperacetals and peracetals and of related bicyclic ozonides

Photolysis and Heterogeneous Reaction of Coniferyl Aldehyde Adsorbed on Silica Particles with Ozone

Ozonolysen von 1‐Methylcyclopenten, 1‐Methylcyclobuten, 5‐Hexen‐2‐on und Naturkautschuk im Beisein von Methanol

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