ArticleScience (New York, N.Y.)2024
A solution to the anti-Bredt olefin synthesis problem.
Article in Science (New York, N.Y.), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Complete Computational Exploration of Eight-Carbon Hydrocarbon Chemical Space.The Journal of organic chemistry · 2026Article
- Rule-breaking in chemical synthesis.Science advances · 2026Review
- strainedSMILES2xyz: a workflow for reliable 3D structures of strained molecules from SMILES.Journal of cheminformatics · 2026Article
- Photochemistry of an Anti-Bredt Olefin through the Lens of Multistate Multireference Quantum Chemistry.Journal of the American Chemical Society · 2026Article
- Hyperpyramidalized alkenes with bond orders near 1.5 as synthetic building blocks.Nature chemistry · 2026Article
- Total Synthesis of Ussuriedine via a Late-Stage Stevens Rearrangement: Implications for Biosynthesis.Journal of the American Chemical Society · 2026Article
- Cafestol-derivatives as potential FXR agonists and CYP7A1 inhibitors and their impact on hypercholesterolemia: an in silico study.Scientific reports · 2026Article
- Towards the selectivity and energetics of anti-Bredt olefins - a density functional theory approach.RSC advances · 2025Article
- Challenging the Bredt's rule in an acid catalyzed cationic cyclization to get bicyclo[3.3.1]nonane derivatives.Nature communications · 2025Article
- Mechanisms of Kobayashi eliminations for the generation of highly strained arynes, cyclic cumulenes, and anti-Bredt olefins.Chemical science · 2025Article
- Geometric distortion as an enabling tool for organic synthesis.Nature synthesis · 2025Article
- Polymers in Physics, Chemistry and Biology: Behavior of Linear Polymers in Fractal Structures.Polymers · 2024Review
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
The π-bonds in unsaturated organic molecules are typically associated with having well-defined geometries that are conserved across diverse structural contexts. Nonetheless, these geometries can be distorted, leading to heightened reactivity of the π-bond. Although π-bond-containing compounds with bent geometries are well utilized in synthetic chemistry, the corresponding leveraging of π-bond-containing compounds that display twisting or pyramidalization remains underdeveloped. We report a study of perhaps the most notorious class of geometrically distorted molecules that contain π-bonds: anti-Bredt olefins (ABOs). ABOs have been known since 1924, and conventional wisdom maintains that ABOs are difficult or impossible to access. We provide a solution to this long-standing problem. Our study also highlights the strategic manipulation of compounds that display considerable distortion arising from the presence of geometrically constrained π-bonds.
Identifiers
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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.