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Cleavage of C=C, C≡C, or N=N bonds with ozone
reacts with this indicator more slowly than with the intended ozonolysis target. The ozonolysis of the indicator, which causes a noticeable color change,
Ozonolysis
Cracks in many different elastomers due to ozone attack
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
Ozone_cracking
Organic compounds of the form >C=O
acylation, the related Houben–Hoesch reaction, and the Fries rearrangement. Ozonolysis, and related dihydroxylation/oxidative sequences, cleave alkenes to give
Ketone
Triatomic oxygen molecule
H2SO4 Alkenes can be oxidatively cleaved by ozone, in a process called ozonolysis, giving alcohols, aldehydes, ketones, and carboxylic acids, depending
Ozone
Class of chemical compounds
Molozonides are formed by cycloaddition of ozone and an alkene during ozonolysis, as a transient intermediate which quickly rearranges to give the ozonide
Molozonide
Chemical compound used to oxidize another substance in a chemical reaction
and CO2 O3 ozone Various, including ketones, aldehydes, and H2O; see ozonolysis F2 fluorine F− Cl2 chlorine Cl− Br2 bromine Br− I2 iodine I−, I− 3 ClO−
Oxidizing_agent
Chemical reaction
aldehyde stage of oxidation and therefore produces the same results as ozonolysis. The classical Lemieux–Johnson oxidation often generates many side products
Lemieux–Johnson_oxidation
German chemist (1866–1923)
During that time he published numerous papers on ozonolysis. His major publication detailing ozonolysis was published in Liebigs Ann. Chem. 1905, 343, 311
Carl_Harries
Chemical compound
Computational evidence also point to the intermediacy of oxirenes in the ozonolysis of alkynes. "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations
Oxirene
Chemical compound
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
Erucic_acid
Use of spectroscopy to investigate and solve problems
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
Applied_spectroscopy
Chemical compound
cholesterol with ozone. Atheronal A (secosterol A) is the major product of ozonolysis which is 3β-hydroxy-5-oxo-5,6-secocholestan-6-al. Atheronal B (secosterol
Atheronals
Chemical compound
mass spectra. Desmosterol has been identified through ozonolysis of the sample, with the ozonolysis product of desmosterol having a melting point of 128 °C
Desmosterol
Alteration in the polymer properties under the influence of environmental factors
styrene-butadiene rubber and NBR being most sensitive to degradation. The ozonolysis reaction results in immediate chain scission. Ozone cracks in products
Polymer_degradation
Polyatomic ion (O3, charge –1), or cyclic compounds made from ozone and alkenes
"Mechanism of Ozonolysis". Angewandte Chemie International Edition in English. 14 (11): 745–752. doi:10.1002/anie.197507451. Ozonolysis mechanism on Organic
Ozonide
Chemical compound
acid was first created in the nineteenth century through the oxidative ozonolysis of Erucic acid. It can yield 2 kinds of salts as it has 2 carboxylic acid
Brassylic_acid
Chemical compound
photo-oxidation; as opposed to other forms of polymer degradation such as ozonolysis. They are also increasingly being used as thermal stabilizers, particularly
Hindered amine light stabilizers
Hindered_amine_light_stabilizers
Stabilizer added to polymeric materials
degradation processes include oxidation, UV-damage, thermal degradation, ozonolysis, combinations thereof such as photo-oxidation, as well as reactions with
Polymer_stabilizer
Carboxylic acid
unsaturation. These reactions are the basis of ozonolysis, hydrogenation, and the iodine number. Ozonolysis (degradation by ozone) is practiced in the production
Fatty_acid
Dicarboxylic acid
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
Maleic_acid
Substance composed of macromolecules with repeating structural units
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
Polymer
Chemical compound
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
Osmium_tetroxide
Organic chemical compound
also inhibits tyrosinase. Azelaic acid is industrially produced by the ozonolysis of oleic acid. The side product is nonanoic acid. It is produced naturally
Azelaic_acid
they are preserved in rocks for millions of years. Monson & Hayes used ozonolysis to characterize the position-specific isotope abundances of unsaturated
Position-specific isotope analysis
Position-specific_isotope_analysis
Chemical compound
ketone of oxetane. Malonic anhydride was first synthesized in 1988 by ozonolysis of diketene. Some derivatives, such as 3,3-dimethyl-oxetane-2,4-dione
Malonic_anhydride
Organic compound containing the functional group R–CH=O
Reaction name Substrate Comment Ozonolysis Alkenes Reductive work-up; similar effect with singlet oxygen and no work-up Carbonyl reduction Esters, amides
Aldehyde
alcohols can be made, depending on the conditions used to process the ozonolysis product. The example below shows the reaction of triolein with ozone and
Natural_oil_polyols
Compound derived from an acid
Hydrolysis of orthoesters in aqueous acid Cellulolysis via esterification Ozonolysis of alkenes using a work up in the presence of hydrochloric acid and various
Ester
Hydrocarbon compound containing one or more C=C bonds
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
Alkene
Naturally occurring psychedelic compound
Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Ozonolysis of elemicin followed by reductive amination. Ester reduction of Eudesmic
Mescaline
Organic compound (CH2(OH)2); simplest geminal diol
decomposition of carbonyl compounds in the atmosphere, and as a product of ozonolysis on these compounds. Methanediol, rather than formaldehyde, is listed as
Methanediol
Chemical compound
affords dimethyl sulfone. Dimethyl sulfide is used in the workup of the ozonolysis of alkenes, where it reduces the intermediate trioxolane. The Swern oxidation
Dimethyl_sulfide
Chemical compound
John E. McMurry, Jack Melton (1977). "Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5-Heptanedione". Organic Syntheses. 56: 36. doi:10.15227/orgsyn
Diisopropylamine
Class of chemical compounds
carbonyl oxide. The latter is known as the Criegee intermediate. The alkene ozonolysis reaction is extremely exothermic, releasing about 50 kilocalories per
Criegee_intermediate
Unsaturated hydrocarbon
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
Monoterpene
Compound that inhibits the oxidation of other molecules
rubber and polybutadiene, are especially susceptible to oxidation and ozonolysis. They can be protected by antiozonants. Oxidation can be accelerated by
Antioxidant
Sudden flow of electric current between two electrically charged objects by contact
essential for nitrogen fixation. Ozone attacks all organic matter by ozonolysis and is used in water purification. Sparks are an ignition source in combustible
Electrostatic_discharge
Dipolar compound with electron delocalization and charge separation over 3 atoms
org/namedreactions/ozonolysis-criegee-mechanism.shtm Ozonolysis mechanism on Organic Chemistry Portal site Li, Jie Jack: Criegee mechanism of ozonolysis Book: Name
1,3-dipole
Electrical device to ionise air molecules
"Quantification of Ozone Levels in Indoor Environments Generated by Ionization and Ozonolysis Air Purifiers" (PDF). Air & Waste Manage. Assoc. 56:601–610. May 2006
Air_ioniser
Chemical compound
refrigerants". Honeywell. 2015. p. 2. McGillen, Max (December 11, 2023). "Ozonolysis can produce long-lived greenhouse gases from commercial refrigerants"
Trans-1,3,3,3-Tetrafluoropropene
Trans-1,3,3,3-Tetrafluoropropene
Chemical compound
Fruekilde, P.; Hjorth, J.; Jensen, N.R.; Kotzias, D.; Larsen, B. (1998). "Ozonolysis at Vegetation Surfaces". Atmospheric Environment. 32 (11): 1893–1902.
Geranylacetone
Chemical compound
methylene group and the formation of several by-products 2-coumaranone. The Ozonolysis of 2-allylphenol obtained by the alkylation of phenol with 3-bromopropene
2-Coumaranone
Organometallic compound (Pb(C2H3O2)4)
2-diols to their corresponding aldehydes or ketones, often replacing ozonolysis; for instance, the oxidation of di-n-butyl d-tartrate to n-butyl glyoxylate
Lead(IV)_acetate
Occupation
implications of secondary organic aerosol production from indoor terpene ozonolysis". Science Advances. 8 (8) eabj9156. Bibcode:2022SciA....8J9156R. doi:10
Floor_cleaning
Chemical reaction
center. Finally, the alkylated ketone or aldehyde can be regenerated by ozonolysis or hydrolysis. This reaction is a useful technique for asymmetric α-alkylation
Enders SAMP/RAMP hydrazone-alkylation reaction
Enders_SAMP/RAMP_hydrazone-alkylation_reaction
Chemical compound (CH2)3(CHO)2
acid-based heteropoly acid catalysts. This reaction essentially mimics ozonolysis. Alternatively it can be made by the Diels-Alder reaction of acrolein
Glutaraldehyde
Chemical compound
doi:10.1016/j.cplett.2007.11.051. McGillen, Max (December 11, 2023). "Ozonolysis can produce long-lived greenhouse gases from commercial refrigerants"
2,3,3,3-Tetrafluoropropene
Fatty acid
Pelargonic acid, similarly to azelaic acid, is produced industrially by the ozonolysis of oleic acid. CH3(CH2)7CH=CH(CH2)7CO2H + O3 → CH3(CH2)7CO2H + HO2C(CH2)7CO2H
Pelargonic_acid
Organosulfur compound (S=C(NH2)2)
corresponding diols. Thiourea is also used in the reductive workup of ozonolysis to give carbonyl compounds. Dimethyl sulfide is also an effective reagent
Thiourea
Parasitic microorganism that causes giardiasis
resistant to conventional water-treatment methods, such as chlorination and ozonolysis. Zoonotic transmission is also possible, but is less frequent. Giardia
Giardia_duodenalis
Monounsaturated omega-9 fatty acid
coatings. Reduction of the carboxylic acid group yields oleyl alcohol. Ozonolysis of oleic acid is an important route to azelaic acid. The coproduct is
Oleic_acid
Device that removes contaminants from the air in a room
"Quantification of Ozone Levels in Indoor Environments Generated by Ionization and Ozonolysis Air Purifiers". Journal of the Air & Waste Management Association. 56
Air_purifier
Chemical reaction
desired aldehyde in situ through ozonolysis, where tin(II) chloride would serve as both the reducing agent in the ozonolysis step as well as the Lewis acid
Roskamp_reaction
Organic compound containing a –C(=O)OH group
such as chromium or manganese oxides. Oxidative cleavage of olefins by ozonolysis, potassium permanganate, or potassium dichromate. Hydrolysis of nitriles
Carboxylic_acid
Microscopic solid or liquid matter suspended in the Earth's atmosphere
Tang, Xiaofeng (1 September 2024). "Ultrafine particles formation from ozonolysis of gas- and particle-phases of cigarette smoke". Atmospheric Environment
Particulate_matter
Polycyclic aromatic hydrocarbon composed of three fused benzene rings
sulfonation to 2 and 3-phenanthrenesulfonic acids with sulfuric acid Ozonolysis to diphenylaldehyde Phenanthrene is extracted from coal tar, of which
Phenanthrene
Sex hormone
2617H. doi:10.1021/ja01162a076. Slomp G (1958). "Ozonolysis. II. 1 The Effect of Pyridine on the Ozonolysis of 4,22-Stigmastadien-3-one 2". Journal of the
Progesterone
condensation, Knoevenagel–Fries modification Hantzsch–Collidin synthesis Harries ozonolysis Haworth methylation Haworth synthesis Hay coupling Hayashi rearrangement
List_of_organic_reactions
Chemical compound
reaction of acetaldehyde oxide, the Criegee intermediate during some ozonolysis reactions. The methyl group helps reduce the rate of ring-opening of the
Methyldioxirane
Chemical compound
Diels-Alder reaction produced a bicyclic compound (7). 7 then underwent ozonolysis to open the six-membered ring leading to selenide (8). 8 was then deselenated
Domoic_acid
Chemical compound
hydrogenation of toluene to methylcyclohexane over ruthenium catalyst. Ozonolysis of 1-methylcyclohexene results in ring-opening. 1-Methylcyclohexene is
1-Methylcyclohexene
Index of chemical compounds with the same name
alkenes, including cycloaddition, formation of epoxides, dihydroxylation, ozonolysis, bromination or hydrogenation. Allyl halides can be used for the preparation
Allyl_halide
Chemical reaction
cyclopropanated, and the carboxylic acid is subsequently deprotected via ozonolysis to form the precursor. The Simmons–Smith reaction is used in the syntheses
Simmons–Smith_reaction
Chemical compound
oxidized to the diacid using nitric acid. An alternative route involves ozonolysis of cyclododecene. Paraffin wax can be converted into DDDA on a laboratory
Dodecanedioic_acid
Chemical compound
Collected Volumes, vol. 2, p. 358. Bailey, Philip S., ed. (1972-06-01). "The Ozonolysis of Organomercurials". Ozone Reactions with Organic Compounds. Advances
2-Bromopropane
Chemical compound
Retrieved January 6, 2026. Bailey, Philip S., ed. (June 1, 1972). "The Ozonolysis of Organomercurials". Ozone Reactions with Organic Compounds. Advances
Diisopropylmercury
Italian atmospheric chemist
quantification of the highly reactive Criegee intermediates produced by ozonolysis reactions in the atmosphere and she studied the impact of aqueous phase
Chiara_Giorio
German chemist (1902–1975)
great achievements was the elucidation of the reaction mechanism for ozonolysis to form Ozonides The Criegee intermediate (or Criegee biradical) and the
Rudolf_Criegee
Chemical compound
686 Å, c = 49.15 Å and β = 53.4° and four formula units per unit cell. Ozonolysis of stearolic acid yields 9,10-dioxostearic acid, having two ketone groups
Stearolic_acid
Chemical compound
"Tri-t-butylsilane: synthesis, physical properties, derivatives, and reactivity towards ozonolysis, chlorination, fluorination, and hydrolysis" Journal of Organometallic
Sodium_silox
N-alkylated and the terminal alkene group is converted into an aldehyde by ozonolysis. This compound is bonded to RP silica gel and this system is subjected
Noncovalent solid-phase organic synthesis
Noncovalent_solid-phase_organic_synthesis
Chemical reaction
presence of ozone. Contrary to their usual roles as intermediates in ozonolysis and other oxidative alkene cleavage reactions, 1,2,4-trioxolanes are relatively
Griesbaum_coozonolysis
Species of fungus
aldehydes from alkenes, representing a biotransformation alternative to ozonolysis. List of Trametes species Arora, David (1986) [1979]. Mushrooms Demystified:
Trametes_hirsuta
Chemical compound
tosyl azide. The ketone then undergoes Wolff rearrangement to ketene 6. Ozonolysis forms the ketone 7, another diazotation yields the diazo ketone 8, which
2.2.2-Propellane
Chemical compound
the laboratory by oxidation of acetaldehyde with selenious acid or by ozonolysis of benzene. Anhydrous glyoxal is prepared by heating solid glyoxal hydrate(s)
Glyoxal
Industrial synthesis of chemical substance
Raney nickel to give lactam H-3c. Destruction of the aromatic ring by ozonolysis, involving the loss of a carboxyl function by spontaneous decarboxylation
Vitamin_B12_total_synthesis
Chemical reaction; acid hydrolysis of a nitroalkane salt to a ketone
McMurry, John E.; Melton, Jack (1977). "Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5-Heptandione". Organic Syntheses. 56: 36. doi:10.15227/orgsyn
Nef_reaction
Reaction in organic chemistry
McMurry, J. E.; Melton, J. (1988). "Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5-Heptanedione". Organic Syntheses; Collected Volumes
Michael_addition_reaction
Chemical synthesis
compound 2 over three steps. Compound 2 was then converted to an aldehyde by ozonolysis and chiral amine 3 was formed in a double reductive amination with (S)-1-phenethylamine
Strychnine_total_synthesis
Chemical compound
Barry Sharpless. Stilbene can be cleanly oxidised to benzaldehyde by ozonolysis or Lemieux–Johnson oxidation, and stronger oxidants such as acidified
(E)-Stilbene
Chemical compound
oxidation of diethyl malonate or its enamines with oxygen or ozone. Thus, the ozonolysis of diethylethylidenmalonate (from malonate and methanal in about 80% yield)
Diethyl_oxomalonate
Branch of forensic engineering
double bonds in their main chains, the group which is attacked during ozonolysis. The problem occurs when small concentrations of ozone gas are present
Forensic materials engineering
Forensic_materials_engineering
Naturally occurring monocyclic sesquiterpene
Winterhalter, R.; Herrmanna, F.; Moortgat, G. K. (2011). "The gas-phase ozonolysis of α-humulene". Physical Chemistry Chemical Physics. 13 (23): 10970–11001
Humulene
Acetic acid bearing an aldehyde group
In addition, the diacid oxalic acid is the main side product. Also, ozonolysis of maleic acid is effective. Glyoxylate is an intermediate of the glyoxylate
Glyoxylic_acid
terminal alkene group of 20 was next converted to a methyl ester using ozonolysis followed by oxidation with potassium permanganate and esterification with
Holton_Taxol_total_synthesis
used as masked enolate equivalents. After addition of the allylsilane, ozonolysis provides the corresponding carbonyl compound. (17) Fleming, I.; Dunogues
Electrophilic substitution of unsaturated silanes
Electrophilic_substitution_of_unsaturated_silanes
Class of chemical compounds
via asymmetric allylboration and silylation of the resulting alcohol. Ozonolysis of the silyl ether and Lindgren–Pinnick oxidation of the aldehyde afforded
Epothilone
Chemical reaction which forms a cyclic molecule
[4+2]-cycloaddition and a 1,3-dipolar addition such as the first step in ozonolysis is a [3+2]-cycloaddition. The IUPAC preferred notation however, with [i+j+
Cycloaddition
Organic compounds of the form R2C=C(R)OOR
reactive intermediates in atmospheric chemistry. They are formed via ozonolysis of alkenes in the atmosphere and form hydroxyl radicals upon decay, which
Alkenyl_peroxides
Photochemical reaction
Shitikova, O. V.; Tolstikov, G. A. (2005). "Ozonolysis of Ricinolic Acid Derivatives and Transformations of the Ozonolysis Products under Barton Reaction Conditions"
Barton_nitrite_ester_reaction
displacement of the bromine atom in prenyl bromide 2 to form diene 3. Ozonolysis of the prenyl group (more electron-rich than the internal double bond)
Wender_Taxol_total_synthesis
Set of rules pertaining to pericyclic reactions
1,3-dipolar cycloaddition of ozone and an olefin in the first step of ozonolysis (a (3+2)-cycloaddition) is [π4s + π2s]. The cheletropic addition of sulfur
Woodward–Hoffmann_rules
Chemical compound
cyclization of the dienone. A regiospecific [3+2] cyclopentannulation, using ozonolysis and an intramolecular aldol condensation, formed the third ring and a
Capnellene
Chemical compound
undergoes fragmentation when treated with benzothiazole-2-thiol to give 2. Ozonolysis (reductive work-up) cleaves the olefinic linkage and the unsymmetrical
Cefroxadine
Chemical compound
side chain and give intermediate 5. Jones oxidation followed in turn by ozonolysis (reductive work-up with zinc-AcOH) and reaction with SOCl2 and pyridine
Latamoxef
Chemical compound
synthesizing photo-leucine requires boc-(S)-photo-leucine, which is prepared via ozonolysis of a commercially available product, followed by formation of the diazirine
L-Photo-leucine
Pericyclic chemical reaction
synthesis of spirotryprostatin A. Ozonolysis is a very important organic reaction. Alkenes and alkynes can be cleaved by ozonolysis to give aldehyde, ketone or
1,3-Dipolar_cycloaddition
Chemical compound
Racemic heleninolic acid can be synthesized starting from methyl oleate. Ozonolysis of this methyl oleate yields methyl 9-oxononanoate. Its carbon chain is
Helenynolic_acid
Methods belonging to this category are extrusion, milling, pyrolysis, ozonolysis, ultrasounds, microwaves, corona and plasma treatments. Chemical treatments
Lignocellulosic filler reinforced polymer
Lignocellulosic_filler_reinforced_polymer
Chemical compound
cleaves double bonds to yield carbonyl products, in a manner similar to ozonolysis. OsO4, a more familiar oxidant that is structurally similar to RuO4, does
Ruthenium_tetroxide
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