Dioxirane Chemistry in Organic Synthesis
Summary
Dioxiranes are three-membered cyclic peroxides characterised by a highly strained O–O bond and marked electrophilicity. Since the pioneering use of dimethyldioxirane for alkene epoxidation, dioxiranes have been exploited as versatile oxidants in metal-free transformations. Their ability to transfer an oxygen atom under mild conditions has enabled selective epoxidation of unactivated alkenes, hydroxylation of activated C–H bonds and oxidative cleavage of olefins. Recent advances have addressed limitations in stability and scalability through in situ generation, immobilisation on solid supports and continuous-flow techniques. Chiral ketone catalysts now permit asymmetric dioxirane formation, delivering enantioenriched epoxides with high selectivity. Applications range from fine-chemical synthesis and natural-product modification to the functionalisation of complex drug candidates. Green-chemistry metrics have improved through the adoption of benign activators such as Oxone and aqueous acetone, while solvent engineering has optimised reaction rates and selectivities. These developments underscore the enduring importance of dioxirane chemistry as a sustainable tool for catalytic oxygen-transfer processes in modern organic synthesis.
Research from Nature Portfolio
No recent Nature Portfolio content available.
Dioxirane Chemistry in Organic Synthesis publication trend
The graph below shows the total number of articles in dioxirane chemistry in organic synthesis across all publications each year (not limited to Nature Index journals).
Technical terms
Dioxirane: A cyclic peroxide with two adjacent oxygen atoms and one carbon atom, used as an electrophilic oxygen-transfer reagent.
Epoxidation: An oxidation reaction converting an alkene to an epoxide by addition of an oxygen atom across the double bond.
Enantioselectivity: The preferential formation of one enantiomer over another in a chiral chemical reaction.
Heterogeneous reagent: A solid-phase catalyst or oxidant that operates in a different phase from the reactants, facilitating separation and reuse.
References
- Selective and metal-free epoxidation of terminal alkenes by heterogeneous polydioxirane in mild conditions. Royal Society Open Science (2018).
- Kinetics of the Epoxidation of Geraniol and Model Systems by Dimethyldioxirane. Molecules (2004).
Turn complex research questions into confident strategic decisions
When you're under pressure to set direction, justify investment, or understand your competitive position, you need more than raw data — you need trusted insights you can act on.
Benchmark your performance against global peers using robust, methodologically sound analysis.
Combine quantitative metrics with qualitative expert insight to uncover strengths, gaps and emerging opportunities.
Gain tailored, decision-ready recommendations aligned to your strategic priorities.
Talk to us to learn more about our data dashboards and bespoke strategy reports.
Grow research skills, confidence and careers with training built for every stage of the research lifecycle.
Developed with Nature Portfolio journal Editors and internationally renowned experts. Discover three ways to learn:
Self-paced, online courses in convenient bite-sized units, covering key skills across scientific writing, publishing, grant writing, data analysis, and more.
Expert trainer-led workshops with hands-on exercises and real-time feedback across core research skills, delivered via interactive group sessions.
Editor-led workshops combining core principles in writing and publishing, personalised 1:1 feedback from Nature Portfolio Editors and hands-on exercises.
Explore course catalogues and workshop agendas, enquire about the options or request institutional pricing.