{ "id": "epgrqcx329", "slug": "epoxidation", "title": "Epoxidation", "updated": "2026-10-15", "topic_path": [ { "id": "physical", "label": "Physical world and mathematics", "api_url": "https://www.edgepedia.org/api/v1/topics/physical" }, { "id": "physical.chemistry", "label": "Chemistry", "api_url": "https://www.edgepedia.org/api/v1/topics/physical.chemistry" }, { "id": "physical.chemistry.methods", "label": "Chemical principles and methods", "api_url": "https://www.edgepedia.org/api/v1/topics/physical.chemistry.methods" }, { "id": "physical.chemistry.methods.chemical-synthesis", "label": "Chemical synthesis", "api_url": "https://www.edgepedia.org/api/v1/topics/physical.chemistry.methods.chemical-synthesis" }, { "id": "physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "label": "Named synthetic methods", "api_url": "https://www.edgepedia.org/api/v1/topics/physical.chemistry.methods.chemical-synthesis.named-preparative-methods" }, { "id": "physical.chemistry.methods.chemical-synthesis.named-preparative-methods.alpha-2-to-he", "label": "Titles 2 to He", "api_url": "https://www.edgepedia.org/api/v1/topics/physical.chemistry.methods.chemical-synthesis.named-preparative-methods.alpha-2-to-he" } ], "geo": [ { "id": "geo.nongeo.t1800.physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "label": "Non-geographic · 1800 to 1945: Named synthetic methods", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1800.physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "path": [ { "id": "geo.nongeo", "label": "Non-geographic", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo" }, { "id": "geo.nongeo.t1800", "label": "Non-geographic · 1800 to 1945", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1800" }, { "id": "geo.nongeo.t1800.physical", "label": "Physical world and mathematics", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1800.physical" }, { "id": "geo.nongeo.t1800.physical.chemistry", "label": "Chemistry", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1800.physical.chemistry" }, { "id": "geo.nongeo.t1800.physical.chemistry.methods", "label": "Chemical principles and methods", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1800.physical.chemistry.methods" }, { "id": "geo.nongeo.t1800.physical.chemistry.methods.chemical-synthesis", "label": "Chemical synthesis", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1800.physical.chemistry.methods.chemical-synthesis" }, { "id": "geo.nongeo.t1800.physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "label": "Named synthetic methods", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1800.physical.chemistry.methods.chemical-synthesis.named-preparative-methods" } ] }, { "id": "geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "label": "Non-geographic · 1946 to 2000: Named synthetic methods", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "path": [ { "id": "geo.nongeo", "label": "Non-geographic", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo" }, { "id": "geo.nongeo.t1946", "label": "Non-geographic · 1946 to 2000", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946" }, { "id": "geo.nongeo.t1946.physical", "label": "Physical world and mathematics", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical" }, { "id": "geo.nongeo.t1946.physical.chemistry", "label": "Chemistry", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical.chemistry" }, { "id": "geo.nongeo.t1946.physical.chemistry.methods", "label": "Chemical principles and methods", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical.chemistry.methods" }, { "id": "geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis", "label": "Chemical synthesis", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis" }, { "id": "geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis.named-preparative-methods", "label": "Named synthetic methods", "api_url": "https://www.edgepedia.org/api/v1/geo/geo.nongeo.t1946.physical.chemistry.methods.chemical-synthesis.named-preparative-methods" } ] } ], "excerpt": "Epoxidation is the chemical conversion of an alkene into an epoxide, a three-membered cyclic ether, by adding a single oxygen atom across the carbon–carbon double bond.", "snippet": "Epoxidation is the chemical conversion of an alkene into an epoxide, a three-membered cyclic ether, by adding a single oxygen atom across the carbon–carbon double bond.", "node": "physical.chemistry.methods.chemical-synthesis.named-preparative-methods.alpha-2-to-he", "markdown": "# Epoxidation\n\nEpoxidation is the chemical conversion of an alkene into an epoxide, a three-membered cyclic ether, by adding a single oxygen atom across the carbon–carbon double bond. Catalytic asymmetric epoxidation with metal-based catalysts (Ti, Mn, V, Mo, and others) is the current method of choice for optically pure epoxides.[1](https://www.sciencedirect.com/science/article/abs/pii/B9780080977744006148) Methods divide broadly into electrophilic oxidants, which attack electron-rich double bonds, and nucleophilic oxidants, which attack electron-poor ones.[1](https://www.sciencedirect.com/science/article/abs/pii/B9780080977744006148)\n\n| Key fact | Detail |\n|---|---|\n| Defining transformation | Alkene + oxygen donor → epoxide (oxirane); peracid version is the Prilezhaev reaction[2](https://www.russchemrev.org/RCR5049pdf) |\n| Stereochemistry | Concerted syn delivery: cis-alkenes give cis-epoxides, trans-alkenes give trans-epoxides[3](https://faculty.csbsju.edu/cschaller/Reactivity/pericyclic/Perioxidation.htm) |\n| Workhorse reagent | m-Chloroperoxybenzoic acid (mCPBA), the most commonly used peracid[2](https://www.russchemrev.org/RCR5049pdf) |\n| Sharpless asymmetric epoxidation | Ti(OiPr)₄, diethyl tartrate, TBHP at −20 °C; 70–87% yield, >90% ee for allylic alcohols[4](https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-0037-1612144.pdf) |\n| Jacobsen–Katsuki epoxidation | Chiral Mn(salen) with NaOCl; extends asymmetric epoxidation to unfunctionalized olefins[2](https://www.russchemrev.org/RCR5049pdf) |\n| Shi epoxidation | Fructose-derived ketone + Oxone generates a chiral dioxirane in situ; pH above 10 raises conversion tenfold[5](https://www.organic-chemistry.org/namedreactions/shi-epoxidation.shtm) |\n| Industrial market share | The co-oxidation route holds the largest market share among propylene oxide epoxidation processes, with the most production lines under construction; HPPO (H₂O₂/TS-1), pioneered by Enichem and commercialized by Evonik and SKC, holds a large share[6](https://www.mdpi.com/1420-3049/30/6/1340) |\n\n## How it works\n\nAll epoxidations transfer an oxygen atom to the alkene π bond, but the oxygen donor and transition state differ by reagent class. With peroxy acids, the two C–O bonds form on the same face of the alkene, so a cis-alkene gives a cis-epoxide and a trans-alkene gives a trans-epoxide, with no opportunity for the stereochemical relationship to change, although the pathway is asynchronous and passes through a post-transition-state intermediate before proton transfer completes the ring.[3](https://faculty.csbsju.edu/cschaller/Reactivity/pericyclic/Perioxidation.htm) Quantum-mechanical reaction-path analysis of propene plus [peracetic acid](https://www.edgepedia.org/peracetic-acid) shows that this single transition state is significantly asynchronous: the first C–O bond forms by nucleophilic attack of the alkene on the electrophilic terminal oxygen with SN2-like O–O bond scission, and a \"hidden intermediate\" forms after the transition state before intramolecular proton transfer completes the ring.[7](https://pmc.ncbi.nlm.nih.gov/articles/PMC6769425/)\n\nMetal-catalyzed variants use high-valent metal–oxo or peroxo species. In TS-1 zeolite catalysis, H₂O₂ is activated by forming titanium peroxocomplexes before the oxygen atom is transferred to the C=C bond.[8](https://doi.org/10.1016/j.isci.2024.109064) In dioxirane epoxidations, the favored transition state is spiro rather than planar, stabilized by an oxygen lone-pair interaction with the alkene \\( \\pi^{*} \\) orbital; kinetic isotope effects on the Shi catalyst confirm an asynchronous transition state with more advanced C–O bond formation at the β-olefinic carbon.[5](https://www.organic-chemistry.org/namedreactions/shi-epoxidation.shtm) • [9](https://pubs.acs.org/jacsat/article/127/18/6679/3516213/Isotope-Effects-and-the-Nature-of)\n\n## How it is done\n\nPeracid protocols treat the alkene with mCPBA.[2](https://www.russchemrev.org/RCR5049pdf) mCPBA is shock sensitive and may explode, so magnesium monoperoxyphthalate (MMPP) was introduced as a safer substitute less prone to thermal decomposition.[10](https://www.ajrconline.org/HTML_Papers/Asian%20Journal%20of%20Research%20in%20Chemistry__PID__2016-9-6-7.html)\n\nSharpless conditions combine Ti(OiPr)₄, a dialkyl tartrate (usually diethyl tartrate), and tert-butyl hydroperoxide in CH₂Cl₂ at −20 °C for about 18 h; selected 1980 examples gave 70–87% yield and >90% ee.[4](https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-0037-1612144.pdf) The active catalyst is a titanium tartrate dimer of proposed C₂ symmetry, with a dominant species of stoichiometry [Ti(OR)₂(tartrate)]ₓ.[11](https://www.degruyter.com/document/doi/10.1351/pac198355111823/pdf)\n\nJacobsen protocol: buffered household bleach (~0.55 M NaOCl adjusted to pH 11.3) is added to the alkene and 10 mol% [Jacobsen's catalyst](https://www.edgepedia.org/jacobsens-catalyst) in dichloromethane at room temperature; reactions typically complete within 2 hours.[12](https://www2.chem.wisc.edu/deptfiles/genchem/Chm346/pdf/41.pdf)\n\nShi conditions: substrate, fructose-derived ketone, Oxone (potassium [peroxymonosulfate](https://www.edgepedia.org/peroxymonosulfate)), and NaHCO₃ in a biphasic medium at 0 °C. The dioxirane forms in situ and the ketone is regenerated, so only catalytic amounts are needed; raising the pH above 10 increased trans-β-methylstyrene conversion tenfold while keeping ee at 90–92%, and also disfavors the Baeyer–Villiger side reaction.[5](https://www.organic-chemistry.org/namedreactions/shi-epoxidation.shtm)\n\nDMDO can be generated continuously in flow from acetone and Oxone, most efficiently at neutral or slightly alkaline pH, avoiding storage of organic peroxides.[13](https://pubs.rsc.org/en/content/articlehtml/2021/py/d0py01676d)\n\n## Origin\n\nThe oxidation of unsaturated compounds with organic peroxides was published by Nikolaus Prileschajew in Berichte der deutschen chemischen Gesellschaft in 1909.[14](https://doi.org/10.1002/cber.190904204100) Early asymmetric attempts with (+)-peroxycamphoric acid gave oxiranes with less than 5% enantiomeric excess, and later peroxide attempts did not exceed about 10% ee.[15](https://www.russchemrev.org/RCR1035pdf) • [16](https://pubs.chemsoc.org.cn/doi/full/10.31635/ccschem.023.202202643) The breakthrough was the 1980 paper by [Tsutomu Katsuki](https://www.edgepedia.org/tsutomu-katsuki) and [K. Barry Sharpless](https://www.edgepedia.org/k-barry-sharpless), titled \"The first practical method for asymmetric epoxidation\", in the [Journal of the American Chemical Society](https://www.edgepedia.org/journal-of-the-american-chemical-society).[17](https://doi.org/10.1021/ja00538a077) Salen-manganese catalysis for unfunctionalized olefins was reported by Wei Zhang and colleagues in the Journal of the American Chemical Society in 1990,[18](https://doi.org/10.1021/ja00163a052) improved with 1,2-diaminocyclohexane-derived catalysts by Eric N. Jacobsen and colleagues in 1991,[19](https://doi.org/10.1021/ja00018a068) and reported independently by Ryo Irie and colleagues in Tetrahedron Asymmetry in 1991.[20](https://doi.org/10.1016/s0957-4166%2800%2986102-9) The catalytic Shi epoxidation was reported by Zhi-Xian Wang and colleagues in the Journal of the American Chemical Society in 1997,[21](https://doi.org/10.1021/ja972272g) with a cis-olefin variant by Hongqi Tian and colleagues in 2000.[22](https://doi.org/10.1021/ja003049d)\n\n## Variants\n\n**Prilezhaev (peracid).** Simple, stereospecific, and chemoselective for electron-rich alkenes; more substituted double bonds can be epoxidized in the presence of less substituted ones, while enones react slowly because the carbonyl makes the alkene electron-poor.[3](https://faculty.csbsju.edu/cschaller/Reactivity/pericyclic/Perioxidation.htm)\n\n**Weitz–Scheffer.** Oxidation of electron-deficient α,β-unsaturated ketones or aldehydes with hydrogen peroxide in basic medium, one of the most commonly applied approaches to epoxide ring formation.[2](https://www.russchemrev.org/RCR5049pdf) The Julia–Colonna asymmetric version of this electron-poor-olefin epoxidation was reported by Stefano Banfi and colleagues in [Tetrahedron](https://www.edgepedia.org/tetrahedron) in 1984,[23](https://doi.org/10.1016/s0040-4020%2801%2991272-4) and organocatalytic asymmetric epoxidation of α,β-unsaturated aldehydes with H₂O₂ was reported by Mauro Marigo and colleagues in the Journal of the American Chemical Society in 2005.[24](https://doi.org/10.1021/ja051808s)\n\n**Sharpless.** Restricted to allylic alcohols, which coordinate the titanium center, but usually delivers >90% ee under mild conditions.[25](https://www.organicreactions.org/pubchapter/asymmetric-epoxidation-of-allylic-alcohols-the-katsuki-sharpless-epoxidation-reaction/) The tartrate configuration is a key determinant of facial selectivity for a given, properly oriented allylic alcohol, while substrate structure and alkene geometry also affect the product's absolute configuration.[2](https://www.russchemrev.org/RCR5049pdf)\n\n**Jacobsen–Katsuki.** Uses NaOCl with chiral Mn(salen) complexes and covers unfunctionalized alkenes, a significant supplement to Sharpless chemistry.[2](https://www.russchemrev.org/RCR5049pdf) A dimeric macrocyclic Mn(III) salen at 2.5 mol% with NaOCl gave enantiopure epoxides of nonfunctionalized alkenes in yields >99% and ee up to 98%, and the catalyst was recycled six times with retained enantioselectivity in styrene epoxidation.[26](https://www.sciencedirect.com/science/article/abs/pii/S0021951711003459) A related Mukaiyama system uses molecular oxygen and an aldehyde with chiral Mn(III) complexes, reported by Tohru Yamada and colleagues in Chemistry Letters in 1992.[27](https://doi.org/10.1246/cl.1992.2231)\n\n**Shi and DMDO.** The Shi ketone, prepared inexpensively from D-fructose, epoxidizes trans-alkenes, allylic and homoallylic alcohols, conjugated dienes, enynes, and unsaturated esters and ethers in high yield and enantioselectivity.[2](https://www.russchemrev.org/RCR5049pdf) Dioxiranes generally are efficient oxygen-transfer reagents that are mild toward substrate and product, and isolated DMDO solutions in acetone oxidize under strictly neutral conditions, useful for acid-labile substrates.[28](https://onlinelibrary.wiley.com/doi/10.1002/0471264180.or061.02)\n\n## Applications\n\n[Propylene oxide](https://www.edgepedia.org/propylene-oxide) is made industrially by the chlorohydrin process, the co-oxidation (hydroperoxide) process, and the [HPPO process](https://www.edgepedia.org/hppo-process), in which TS-1 zeolite catalyzes epoxidation with H₂O₂. HPPO has advantages in by-products and environmental friendliness: the chlorohydrin route forms harmful salt chloride side products, while hydroperoxide routes produce styrene, tert-butyl alcohol, and dimethyl benzyl alcohol as coproducts.[8](https://doi.org/10.1016/j.isci.2024.109064) HPPO, pioneered by Enichem and first commercialized by Evonik and SKC, offers a simple flow, mild conditions, high yield, and no waste residue; the co-oxidation method nonetheless holds the largest market share and the most production lines under construction.[6](https://www.mdpi.com/1420-3049/30/6/1340) [Ethylene oxide](https://www.edgepedia.org/ethylene-oxide) is made by direct silver-catalyzed oxidation of ethylene and is used for ethylene glycol, glycol ethers, and ethanolamines, while propylene oxide is mainly consumed for polyether polyols in polyurethane foams.[6](https://www.mdpi.com/1420-3049/30/6/1340) • [16](https://pubs.chemsoc.org.cn/doi/full/10.31635/ccschem.023.202202643)\n\n## Limitations and alternatives\n\nEach named method has a defined limit: classical [Sharpless epoxidation](https://www.edgepedia.org/sharpless-epoxidation) requires an allylic alcohol and is unsuitable for unfunctionalized alkenes in that form,[2](https://www.russchemrev.org/RCR5049pdf) the Shi reaction is sensitive to medium pH because the catalyst decomposes outside a workable range,[2](https://www.russchemrev.org/RCR5049pdf) and homogeneous Mn(salen) catalysts pose regeneration problems, motivating heterogeneous versions on solid supports.[2](https://www.russchemrev.org/RCR5049pdf) Electron-poor alkenes need nucleophilic oxidants such as the Weitz–Scheffer system, since electrophilic peracids are slow on enones.[3](https://faculty.csbsju.edu/cschaller/Reactivity/pericyclic/Perioxidation.htm) Side reactions include Baeyer–[Villiger oxidation](https://www.edgepedia.org/villiger-oxidation) of the peracid or ketone catalyst, disfavored at pH above 10 in the Shi system,[5](https://www.organic-chemistry.org/namedreactions/shi-epoxidation.shtm) and acid-catalyzed epoxide opening, which neutral dioxirane conditions avoid.[28](https://onlinelibrary.wiley.com/doi/10.1002/0471264180.or061.02) Biocatalytic routes, including direct epoxidation by monooxygenases and indirect epoxide hydrolysis, offer enantiopure epoxides as an alternative to chemical catalysis.[29](https://www.annualreviews.org/content/journals/10.1146/annurev.micro.51.1.491) Cytochrome P450 enzymes epoxidize double bonds using O₂ or H₂O₂, through either a concerted pathway from the Fe(III)–OOH intermediate or a radical pathway via compound I, and engineered enzymes such as CHMO epoxidize vinyl phosphonates with >98% ee, although a biocatalyst combining broad scope, no kinetic resolution, and activity on unactivated terminal alkenes remains elusive.[30](https://www.cell.com/cell-reports-physical-science/fulltext/S2666-3864%2825%2900393-5) In electrochemistry, a halogen-free cobalt-based perovskite anode achieved direct aqueous electrochemical epoxidation of propylene, previously shown only on noble metals unstable outside halogenated electrolytes.[31](https://www.nature.com/articles/s41929-026-01535-6)\n\n## References\n\n1. [Asymmetric Epoxidation and Sulfoxidation (Burke & Carreiro, Comprehensive Inorganic Chemistry II, 2013)](https://www.sciencedirect.com/science/article/abs/pii/B9780080977744006148)\n2. [Epoxides: methods of synthesis, reactivity, practical significance (Russian Chemical Reviews)](https://www.russchemrev.org/RCR5049pdf)\n3. [Reactivity: Alkene Oxidation (CSB/SJU organic chemistry text, Schaller)](https://faculty.csbsju.edu/cschaller/Reactivity/pericyclic/Perioxidation.htm)\n4. [The Sharpless Epoxidation (SYNFACTS synopsis of Katsuki & Sharpless 1980)](https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-0037-1612144.pdf)\n5. [Shi Epoxidation (Organic Chemistry Portal named reaction page)](https://www.organic-chemistry.org/namedreactions/shi-epoxidation.shtm)\n6. [Research Progress in Epoxidation of Light Small-Molecule Olefins](https://www.mdpi.com/1420-3049/30/6/1340)\n7. [Epoxidation of Alkenes by Peracids: From Textbook Mechanisms to a Quantum Mechanically Derived Curly-Arrow Depiction](https://pmc.ncbi.nlm.nih.gov/articles/PMC6769425/)\n8. [Review and perspectives on TS-1 catalyzed propylene epoxidation (iScience, 2024)](https://doi.org/10.1016/j.isci.2024.109064)\n9. [Isotope Effects and the Nature of Enantioselectivity in the Shi Epoxidation. The Importance of Asynchronicity (Singleton & Wang, JACS 2005)](https://pubs.acs.org/jacsat/article/127/18/6679/3516213/Isotope-Effects-and-the-Nature-of)\n10. [Epoxidation and the Sharpless asymmetric epoxidation (Asian Journal of Research in Chemistry)](https://www.ajrconline.org/HTML_Papers/Asian%20Journal%20of%20Research%20in%20Chemistry__PID__2016-9-6-7.html)\n11. [On the Mechanism of Titanium–Tartrate Catalyzed Asymmetric Epoxidation](https://www.degruyter.com/document/doi/10.1351/pac198355111823/pdf)\n12. [Experiment #3: Asymmetric Epoxidation, The Use of a Chiral Catalyst for the Enantioselective Epoxidation of Alkenes](https://www2.chem.wisc.edu/deptfiles/genchem/Chm346/pdf/41.pdf)\n13. [Continuous dimethyldioxirane generation for polymer epoxidation](https://pubs.rsc.org/en/content/articlehtml/2021/py/d0py01676d)\n14. [Nikolaus Prileschajew (1909). Oxydation ungesättigter Verbindungen mittels organischer Superoxyde. Berichte der deutschen chemischen Gesellschaft.](https://doi.org/10.1002/cber.190904204100)\n15. [Asymmetric epoxidation (Russian Chemical Reviews historical review)](https://www.russchemrev.org/RCR1035pdf)\n16. [Advances in Electrochemical Oxidation of Olefins to Epoxides](https://pubs.chemsoc.org.cn/doi/full/10.31635/ccschem.023.202202643)\n17. [Tsutomu Katsuki, K. Barry Sharpless (1980). The first practical method for asymmetric epoxidation. Journal of the American Chemical Society.](https://doi.org/10.1021/ja00538a077)\n18. [Wei Zhang and colleagues (1990). Enantioselective epoxidation of unfunctionalized olefins catalyzed by salen manganese complexes. Journal of the American Chemical Society.](https://doi.org/10.1021/ja00163a052)\n19. [Eric N. Jacobsen and colleagues (1991). Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane. Journal of the American Chemical Society.](https://doi.org/10.1021/ja00018a068)\n20. [Catalytic asymmetric epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes (Tetrahedron Asymmetry, 1991)](https://doi.org/10.1016/s0957-4166%2800%2986102-9)\n21. [Zhi-Xian Wang and colleagues (1997). An Efficient Catalytic Asymmetric Epoxidation Method. Journal of the American Chemical Society.](https://doi.org/10.1021/ja972272g)\n22. [Hongqi Tian and colleagues (2000). Highly Enantioselective Epoxidation of cis-Olefins by Chiral Dioxirane. Journal of the American Chemical Society.](https://doi.org/10.1021/ja003049d)\n23. [Asymmetric epoxidation of electron-poor olefins-V (Tetrahedron, 1984)](https://doi.org/10.1016/s0040-4020%2801%2991272-4)\n24. [Mauro Marigo and colleagues (2005). Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes with Hydrogen Peroxide. Journal of the American Chemical Society.](https://doi.org/10.1021/ja051808s)\n25. [Asymmetric Epoxidation of Allylic Alcohols: The Katsuki-Sharpless Epoxidation Reaction (Organic Reactions, Vol. 48)](https://www.organicreactions.org/pubchapter/asymmetric-epoxidation-of-allylic-alcohols-the-katsuki-sharpless-epoxidation-reaction/)\n26. [Reusable chiral macrocyclic Mn(III) salen complexes for enantioselective epoxidation of nonfunctionalized alkenes](https://www.sciencedirect.com/science/article/abs/pii/S0021951711003459)\n27. [Tohru Yamada and colleagues (1992). Enantioselective Epoxidation of Unfunctionalized Olefins with Molecular Oxygen and Aldehyde Catalyzed by Optically Active Manganese(III) Complexes. Chemistry Letters.](https://doi.org/10.1246/cl.1992.2231)\n28. [Organic Reactions chapter: Dioxirane epoxidation of carbon-carbon double bonds](https://onlinelibrary.wiley.com/doi/10.1002/0471264180.or061.02)\n29. [Synthesis of Enantiopure Epoxides through Biocatalytic Approaches (Archelas & Furstoss, Annual Review of Microbiology 1997)](https://www.annualreviews.org/content/journals/10.1146/annurev.micro.51.1.491)\n30. [Enzymatic epoxidation strategies for the stereoselective synthesis of chiral epoxides](https://www.cell.com/cell-reports-physical-science/fulltext/S2666-3864%2825%2900393-5)\n31. [Direct electrochemical propylene epoxidation over amorphized perovskite oxide in non-halogenated aqueous electrolyte](https://www.nature.com/articles/s41929-026-01535-6)\n\n---\n*Topic: Encyclopedia › Physical world and mathematics › Chemistry › Chemical principles and methods › Chemical synthesis › Named synthetic methods › Titles 2 to He*\n\n*Initially written Sep 29, 2026 · Edited: Oct 15, 2026*\n\n*Copyright 2026 EdgeChat AI, a subsidiary of Biostate AI.*\n\nLicense: Edgepedia Community License 1.0, https://www.edgepedia.org/edgepedia/license\n", "same_as": [], "url": "https://www.edgepedia.org/epoxidation", "markdown_url": "https://www.edgepedia.org/epoxidation.md", "license": { "name": "Edgepedia Community License 1.0", "url": "https://www.edgepedia.org/edgepedia/license", "summary": "Free with credit, commercial use included. AI training is open to everyone. For other uses, organizations over USD 100M in revenue or 100M monthly users license separately.", "spdx": "LicenseRef-Edgepedia-Community-1.0" }, "credit": "\"Epoxidation\", Edgepedia (EdgeChat), https://www.edgepedia.org/epoxidation. Edgepedia Community License 1.0.", "credit_md": "\"[Epoxidation](https://www.edgepedia.org/epoxidation)\", Edgepedia (EdgeChat), [https://www.edgepedia.org/epoxidation](https://www.edgepedia.org/epoxidation). [Edgepedia Community License 1.0](https://www.edgepedia.org/edgepedia/license).", "credit_html": "\"Epoxidation\", Edgepedia (EdgeChat), https://www.edgepedia.org/epoxidation. Edgepedia Community License 1.0.", "speakable": "Epoxidation is the chemical conversion of an alkene into an epoxide, a three-membered cyclic ether, by adding a single oxygen atom across the carbon–carbon double bond." }