Mechanism of Ozonation Reactions. Nitrones

Erickson, Ronald E.; Myszkiewicz, Thomas M.

doi:10.1021/jo01023a513

Cited by 13 publications

(4 citation statements)

References 3 publications

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“…However, it should not be concluded that all ozone reactions necessarily proceed by such a mechanism. In other cases where ionic intermediates are more favored (e.g., in more polar solvents or in cases where carbonium ions are more stable) it is possible that the tran sition state for the reaction has more polar character (9,10,27 Enzymic hydroxylations of saturated hydrocarbons, which apparently involve the insertion of an oxygen to give alcohols with retention of con figuration, could presumably occur by a mechanism similar to that pro posed for the ozonation reaction. In the enzymic reactions oxygen is the oxidant, and the over-all mechanism is clearly more complicated than that for ozonation (II).…”

Section: Ro-+ Rh -> R-+ Roh (Retention)mentioning

confidence: 99%

The Mechanism of Alkane Oxidation by Ozone

Hamilton

Ribner

Hellman

1968

Advances in Chemistry

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The characteristics of the initial step in the reaction of ozone with saturated hydrocarbons have been investigated. Ozonation of cyclohexane gives initially cyclohexanol and cyclohexanone in a 3:1 ratio. Cyclohexane is oxidized 4.5 times more rapidly than cyclohexane-d 12 . The relative reactivity of primary, secondary, and tertiary hydrogens is approximately 1:13:110. The ozonation of tertiary hydrogens to tertiary alcohols occurs with 60 to 70% retention of configuration. The presence of good hydrogen atom donors, antioxidants, and a number of other reagents has only a small effect on the percent retention of configuration. These results and others are compared with those obtained for other hydrocarbon reactions, and a mechanism for the ozonation is suggested. Asa result of our interest in the mechanism of biological oxidations of saturated hydrocarbons (II), we have investigated the mechanisms of several alkane oxidations (12, 13). This paper reports our studies on the oxidation of saturated hydrocarbons by ozone. Although there are frequent references in the literature to the oxidation of alkanes by ozone(2), the mechanism of the reaction has received relatively little study.Durland and Adkins (7) reported that cis-and Jrans-Decalin are oxidized in reasonable yield to tertiary alcohols with retention of configuration.Schubert and Pease (24) studied the gas-phase ozonation of alkanes at room temperature and suggested that the products arose from the forma tion and further reactions of RO' and HOO*. A complicating feature in these investigations was the necessity to carry out the oxidation to rela tively high conversions so that the products could be analyzed. Since 15 Downloaded by MICHIGAN STATE UNIV on February 19, 2015 |

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Section: Ro-+ Rh -> R-+ Roh (Retention)mentioning

confidence: 99%

The Mechanism of Alkane Oxidation by Ozone

Hamilton

Ribner

Hellman

1968

Advances in Chemistry

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“…Soc., 89, 1515 (1967). 6 Determined vs. benzyl /-butyl ether at -78°. c Determined vs. dibutyl ether.…”

Section: Resultsmentioning

confidence: 99%

“…1.0 0.5 °Measured as mole ratios. 6 Relative amount of -butyl alcohol dependent on degree of completion of ozonation. Relative percentage of /-butyl alcohol increases while relative percentage of /-butyl acetate decreases slightly during the course of the reaction.…”

Section: Discussionmentioning

confidence: 99%

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Mechanism of ozonation reactions. III. Ethers

Erickson¹,

Hansen²,

Harkins³

1968

J. Am. Chem. Soc.

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A study of the mechanism of the ozonation of ethers has been carried out utilizing isotope effect rate studies, competitive relative rate studies on various classes of ethers, and product analysis of ozonations using ozone-oxygen and ozone-nitrogen streams. Results are discussed in terms of both the mode of initial attack of ozone on the system and the varieties of decomposition available to the hydrotrioxide intermediate I. The over-all mechanism is a complicated one involving free radical autoxidation when oxygen is present.

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Ozone

Kirschner¹

2000

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Physical Properties 3. Chemical Properties 4. Production 5. Environmental Protection 6. Analysis 7. Uses 7.1. Potable Water Filtration and Disinfection 7.2. Wastewater Treatment 7.3. Other Uses 8. Toxicology and Occupational Health

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Mechanism of Ozonation Reactions. Nitrones

Cited by 13 publications

References 3 publications

The Mechanism of Alkane Oxidation by Ozone

The Mechanism of Alkane Oxidation by Ozone

Mechanism of ozonation reactions. III. Ethers

Ozone

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