Complexes and Radicals Produced during Ozonation of Olefins

Bailey, Philip S.; Ward, James W.; Hornish, Rex E.; Potts, Fred E.

doi:10.1021/ba-1972-0112.ch001

Cited by 23 publications

(5 citation statements)

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“…The charge-transfer complexes have been suggested to be formed in the low-temperature ozonations of mesitylene, 1-mesityl-1-phenylethylene, and 1-methoxy-1,2,2-trimesitylethylene …”

Section: Resultsmentioning

confidence: 99%

“…The wavelengths of the visible absorption spectra for the aromatic ozonations have been shown to gradually increase as the number of the alkyl substitutions of the double bond increases. This could be attributed to the electron-donating properties of the alkyl substituents, which can stabilize the radical cation intermediates formed and shift the absorption to the red side 22b…”

Section: Resultsmentioning

confidence: 99%

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Olefinic Ozonation Electron Transfer Mechanism

Zhang

Zhu²

1997

J. Org. Chem.

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Ozonations of ammonia, amines, anilines, and p-phenylenediamines have been shown to proceed via an electron transfer reaction mechanism. The ozonation rate constants for the alkenes with different substituents were shown to be linearly correlated with the ionization potentials of the corresponding olefinic substrates. The rate constants for the ozonations of methyl-substituted benzenes were also shown to be linearly correlated with the ionization potentials of the corresponding aromatic substrates. These results together with other related experimental evidences lead us to suggest that the olefinic ozonations proceed via an electron transfer reaction mechanism (Scheme ). This mechanism explains why the derivatives of p-phenylenediamine can be used as efficient antiozonants to prevent the degradation of rubber products caused by ozone.

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“…The charge-transfer complexes have been suggested to be formed in the low-temperature ozonations of mesitylene, 1-mesityl-1-phenylethylene, and 1-methoxy-1,2,2-trimesitylethylene …”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Olefinic Ozonation Electron Transfer Mechanism

Zhang

Zhu²

1997

J. Org. Chem.

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“…According to the generally accepted mechanism (Criegee 1957;Baüey 1958) The Chemistry of Delignification, Part II 59 ozonide", a 1,2,3-trioxacyclopentane, fragments to form a simple carbonyl compound and a caibonyl oxide or zwitterion. The latter lose one molecule of oxygen to yield the corresponding epoxides (Bailey and Lane 1967;Bailey et al 1972). Olefins may also und ergo 1,1-cycloaddition of ozone via π-and σ-complexes (3).…”

Section: ) Oxidation Of Aromatic and Oleflnic Structures By Ozonementioning

confidence: 99%

The Chemistry of Delignification - A General Concept - Part II

Gierer¹

1982

Holzforschung

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“…Story et al103 have also included type 65 and 66 reactions in their ozonolysis mechanism but not as a reversible step 65. Bailey et al 104 have described the 66-type reaction as a 1,3dipolar cycloaddition and have included additional decay steps for the ir complex to account for the expoxides and free radical products observed in many ozonolysis reactions. These additional steps in the present case would be as follows.…”

Section: B Review Of Ozonolysis Mechanismsmentioning

confidence: 99%