ArticleThe Journal of organic chemistry2024
Beyond Strain Release: Delocalization-Enabled Organic Reactivity.
Article in The Journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Catalytic Transformations of Aza-Cyclobutenes, Fused Cyclobutenes, and Cyclobutenones.Chemical record (New York, N.Y.) · 2026Review
- A Scalable Stereoselective Synthesis of Polysubstituted Housanes.Organic letters · 2026Article
- Regio- and Stereoselective Deprotonation and Functionalization of Strained 1-Aza[n.1.0]bicycles.Journal of the American Chemical Society · 2026Article
- Hyperpyramidalized alkenes with bond orders near 1.5 as synthetic building blocks.Nature chemistry · 2026Article
- Transition Metal-Catalyzed Direct C(spChemical reviews · 2026Review
- Electrochemical Activation of Bicyclo[1.1.0]butanes.Organic letters · 2026Article
- Asymmetric Carbonium Ion Catalysis: The Intramolecular Hydroalkoxylation of Cyclopropanes.Journal of the American Chemical Society · 2026Article
- Boron-Enabled Stereoselective Synthesis of Polysubstituted Housanes.Journal of the American Chemical Society · 2025Article
- Fast and Accurate Ring Strain Energy Predictions with Machine Learning and Application in Strain-Promoted Reactions.JACS Au · 2025Article
- SmIAngewandte Chemie (International ed. in English) · 2025Article
- DirectJournal of the American Chemical Society · 2025Article
- Understanding Bio-Orthogonal Strain-Driven Sydnone Cycloadditions: Data-Assisted Profiles and the Search for Linear Relationships.Molecules (Basel, Switzerland) · 2025Article
- Article
- A solution to the anti-Bredt olefin synthesis problem.Science (New York, N.Y.) · 2024Article
- Controlled oligomerization of [1.1.1]propellane through radical polarity matching: selective synthesis of SFBeilstein journal of organic chemistry · 2024Article
- One-Pot Synthesis of Strain-Release Reagents from Methyl Sulfones.Journal of the American Chemical Society · 2022Article
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The release of strain energy is a fundamental driving force for organic reactions. However, absolute strain energy alone is an insufficient predictor of reactivity, evidenced by the similar ring strain but disparate reactivity of cyclopropanes and cyclobutanes. In this work, we demonstrate that electronic delocalization is a key factor that operates alongside strain release to boost, or even dominate, reactivity. This delocalization principle extends across a wide range of molecules containing three-membered rings such as epoxides, aziridines, and propellanes and also applies to strain-driven cycloaddition reactions. Our findings lead to a "rule of thumb" for the accurate prediction of activation barriers in such systems, which can be easily applied to reactions involving many of the strained building blocks commonly encountered in organic synthesis, medicinal chemistry, polymer science, and bioconjugation. Given the significance of electronic delocalization in organic chemistry, for example in aromatic π-systems and hyperconjugation, we anticipate that this concept will serve as a versatile tool to understand and predict organic reactivity.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.