Ozonation of Aromatic Aldehydes<sup>1</sup>

White, Harold M.; Bailey, Philip S.

doi:10.1021/jo01020a035

Cited by 55 publications

(38 citation statements)

References 1 publication

(2 reference statements)

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“…Most of the infrared runs were performed in CH 2 (5) led to a considerable (more than one order of magnitude) decrease in CL intensity in both spectral ranges.…”

Section: Chemiluminescence Kinetics On Thermal Decomposition Of Hydromentioning

confidence: 99%

“…[1][2][3][4] HTs including a wide range of O-and Si-containing compounds (alcohols, ethers, acetals, aldehydes, silanes, etc.) have been synthesized and examined since then.…”

Section: Introductionmentioning

confidence: 99%

“…The first rapid region represents adduct A depletion in reactions (1) and (2). The next slow region corresponds to full conversion of A into B and represents the decomposition kinetics of the latter.…”

mentioning

confidence: 99%

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Formation of hydrotrioxides during ozonation of hydrocarbons on silica gel. Decomposition of hydrotrioxides

Avzyanova

Timerghazin

Khalizov

et al. 2000

J. Phys. Org. Chem.

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Hydrotrioxides (HT), ROOOH, from isopentane, 1,4-dimethylcyclohexane, 1,3-dimethylcyclohexane, decalin and triphenylmethane were synthesized for the first time by low-temperature ozonation of the corresponding hydrocarbons on a silica surface. Thermal decomposition of hydrotrioxides is accompanied by the formation of radicals and by infrared and visible chemiluminescence (CL). In solution the HTs form self-associates and react reversibly with the solvent (acetone) producing Bayer-Villiger type intermediates (unsymmetrical dialkyl trioxides). These reactions cause a complex character of the decomposition kinetics of HTs, as evidenced by monitoring the dependence of CL intensity on time. Activation parameters of thermal decomposition of HTs show a compensation effect (logA vs E A ) which describes well the available experimental and theoretical data for the homolysis of organic trioxides.

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“…Most of the infrared runs were performed in CH 2 (5) led to a considerable (more than one order of magnitude) decrease in CL intensity in both spectral ranges.…”

Section: Chemiluminescence Kinetics On Thermal Decomposition Of Hydromentioning

confidence: 99%

“…[1][2][3][4] HTs including a wide range of O-and Si-containing compounds (alcohols, ethers, acetals, aldehydes, silanes, etc.) have been synthesized and examined since then.…”

Section: Introductionmentioning

confidence: 99%

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Formation of hydrotrioxides during ozonation of hydrocarbons on silica gel. Decomposition of hydrotrioxides

Avzyanova

Timerghazin

Khalizov

et al. 2000

J. Phys. Org. Chem.

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“…Antiperiplanar lone pairs will elongate the C-H bond as well as stabilize the incipient dioxonium ion. The 1,3-diplolar insertion mechanism (Scheme 3b) has been postulated for the ozonation of ethers (10)(11)(12), aldehydes (13,14), and hydrocarbons (15,16). Ozone attack on oxygen (Scheme 3c) is similar to that proposed for the ozonation of certain amines (18), and ethers (12).…”

Section: Substituent Effectsmentioning

confidence: 99%

The mechanism of oxidation of acetals by ozone. I. Stoichiometry, order of the reaction, solvent effects, and substituent effects

Taillefer¹,

Thomas²,

Nadeau³

et al. 1980

Can. J. Chem.

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A systematic investigation of the reaction between ozone and acetals to form acetal hydrotrioxides A has been undertaken. The stoichiometry of the reaction has been shown to be 1:l in each reactant and the order of the reaction was also one in each reactant. Substituent effects measured in a variety of systems and under several conditions of temperature and solvent were found to be small (p = -1.10 to -1.58). Solvent polarity was also found to have little effect on the rate of the reaction. Mechanistically, these facts are interpreted in terms of a 1.3-dipolar insertion of ozone into the C-H bond of the acetal function.ROLAND J. TAILLEFER, SHIRLEY E. THOMAS, YVES NADEAU, S. FLISZAR et HERVE HENRY. Can. J. Chem. 58, 1138Chem. 58, (1980. Une etude systematique de la rtaction de I'ozone avec les acetals pour former les acktals hydrotrioxides A a t t t entreprise. On a trouve que la stoechiomttrie et I'ordre de la reaction etaient de un dans chacun des reactifs. L'effet des substituents sur la vitesse de reaction, mesure dans plusieurs systimes et sous difftrentes conditions de temperatures et de solvants est faible (p = -1.108 -1.58) de mime que I'effet de la polarit6 des solvants. Ces faits sont interpretis en invoquant un mecanisme d'addition 1,3-dipolaire de I'ozone dans le lien C-H de la fonction acetale.

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“…More recently, however, evidence has indicated that ozone reacts with the saturated carbon-hydrogen bond of alkanes, as well as with ethers, aldehydes, and acetals by a concerted reaction involving the 1,3-dipolar insertion of the ozone molecule into the carbon-hydrogen bond (10,(108)(109)(110)(111)(112)(113)(114)(115)(116)(117)(118)(119)(120) . This mechanism was originally suggested by Price and Tumolo (108) •H…”

Section: Gc-ms Gc-ftirmentioning

confidence: 99%

Comparison of the ozonolysis products of the methylnaphthalenes and dimethylnaphthalenes in hexane, methanol, and water

Gaul

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Ozonation of Aromatic Aldehydes¹

Cited by 55 publications

References 1 publication

Formation of hydrotrioxides during ozonation of hydrocarbons on silica gel. Decomposition of hydrotrioxides

Formation of hydrotrioxides during ozonation of hydrocarbons on silica gel. Decomposition of hydrotrioxides

The mechanism of oxidation of acetals by ozone. I. Stoichiometry, order of the reaction, solvent effects, and substituent effects

Comparison of the ozonolysis products of the methylnaphthalenes and dimethylnaphthalenes in hexane, methanol, and water

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Ozonation of Aromatic Aldehydes1

Cited by 55 publications

References 1 publication

Formation of hydrotrioxides during ozonation of hydrocarbons on silica gel. Decomposition of hydrotrioxides

Formation of hydrotrioxides during ozonation of hydrocarbons on silica gel. Decomposition of hydrotrioxides

The mechanism of oxidation of acetals by ozone. I. Stoichiometry, order of the reaction, solvent effects, and substituent effects

Comparison of the ozonolysis products of the methylnaphthalenes and dimethylnaphthalenes in hexane, methanol, and water

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Ozonation of Aromatic Aldehydes¹