In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds are cleaved with ozone (O3). Multiple carbon–carbon bond are replaced by carbonyl (C=O) groups, such as aldehydes, ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage. The outcome of the reaction depends on the type of multiple bond being oxidized and the work-up conditions.[1]
Detailed procedures have been reported.[2][3][4]
^Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 1036, ISBN 978-0-471-72091-1
^Bailey, P. S.; Erickson, R. E. (1973). "Diphenaldehyde". Organic Syntheses; Collected Volumes, vol. 5, p. 489.
^Tietze, L. F.; Bratz, M. (1998). "Dialkyl Mesoxalates by Ozonolysis of Dialkyl Benzalmalonates". Organic Syntheses; Collected Volumes, vol. 9, p. 314.
^Harwood, Laurence M.; Moody, Christopher J. (1989). Experimental Organic Chemistry: Principles and Practice (Illustrated ed.). Wiley-Blackwell. pp. 55–57. ISBN 978-0632020171.
reacts with this indicator more slowly than with the intended ozonolysis target. The ozonolysis of the indicator, which causes a noticeable color change,...
resolution. The reaction occurring between double bonds and ozone is known as ozonolysis when one molecule of the gas reacts with the double bond: The immediate...
In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally...
unstable endoperoxide. Thiourea is also used in the reductive workup of ozonolysis to give carbonyl compounds. Dimethyl sulfide is also an effective reagent...
"Mechanism of Ozonolysis". Angewandte Chemie International Edition in English. 14 (11): 745–752. doi:10.1002/anie.197507451. Ozonolysis mechanism on Organic...
chloro(dimethyl sulfide)gold(I). Dimethyl sulfide is used in the workup of the ozonolysis of alkenes. It reduces the intermediate trioxolane. The Swern oxidation...
affected. The reaction occurring between double bonds and ozone is known as ozonolysis when one molecule of the gas reacts with the double bond: The immediate...
styrene-butadiene rubber and NBR being most sensitive to degradation. The ozonolysis reaction results in immediate chain scission. Ozone cracks in products...
mass spectra. Desmosterol has been identified through ozonolysis of the sample, with the ozonolysis product of desmosterol having a melting point of 128 °C...
H2SO4}}\end{aligned}}} Alkenes can be oxidatively cleaved by ozone, in a process called ozonolysis, giving alcohols, aldehydes, ketones, and carboxylic acids, depending...
acylation, the related Houben–Hoesch reaction, and the Fries rearrangement. Ozonolysis, and related dihydroxylation/oxidative sequences, cleave alkenes to give...
Hydrolysis of orthoesters in aqueous acid Cellulolysis via esterification Ozonolysis of alkenes using a work up in the presence of hydrochloric acid and various...
Molozonides are formed by cycloaddition of ozone and an alkene during ozonolysis, as a transient intermediate which quickly rearranges to give the ozonide...
Reaction name Substrate Comment Ozonolysis Alkenes Reductive work-up; similar effect with singlet oxygen and no work-up Carbonyl reduction Esters, amides...
the catalytic loading of OsO4. This process is equivalent to that of ozonolysis. OsO4 is a Lewis acid and a mild oxidant. It reacts with alkaline aqueous...
is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid may be used to form acid addition salts with drugs to make...
oxidizing agents, including the strong oxidizing agent ozone, undergoing ozonolysis to release either atomic oxygen or a hydroxyl radical. Its reactivity...
used to make specialty polyamides and polyesters. The conversion entails ozonolysis, which selectively cleaves the C=C bond in erucic acid: CH3(CH2)7CH=CH(CH2)11CO2H...
ozone, leading to the scission of the double bond. The process is called ozonolysis. Often the reaction procedure includes a mild reductant, such as dimethylsulfide...
"Quantification of Ozone Levels in Indoor Environments Generated by Ionization and Ozonolysis Air Purifiers" (PDF). Air & Waste Manage. Assoc. 56:601–610. May 2006...
rubber and polybutadiene, are especially susceptible to oxidation and ozonolysis. They can be protected by antiozonants. Oxidation can be accelerated by...
They possess double bonds in their repeat units which are cleaved during ozonolysis. Cracks in fuel lines can penetrate the bore of the tube and cause fuel...
respiratory tracts when the time is spent near a busy road. This is due to ozonolysis of monoterpenes like Limonene leading to the production of atmospheric...
Computational evidence also point to the intermediacy of oxirenes in the ozonolysis of alkynes. "Front Matter". Nomenclature of Organic Chemistry : IUPAC...
sulfonation to 2 and 3-phenanthrenesulfonic acids with sulfuric acid Ozonolysis to diphenylaldehyde Phenanthrene is more stable than its linear isomer...
or manganese oxides.[citation needed] Oxidative cleavage of olefins by ozonolysis, potassium permanganate, or potassium dichromate. Hydrolysis of nitriles...
acid-based heteropoly acid catalysts. This reaction essentially mimics ozonolysis. Alternatively it can be made by the Diels-Alder reaction of acrolein...
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