2024/10/31 by Luca McDermott, Zach G. Walters, Sarah A. French +5 · 1 voice · 1 citation
Biochemistry, Genetics and Molecular Biology · Chemistry · #Chemical Synthesis and Analysis #Cyclization and Aryne Chemistry #Organic Chemistry Cycloaddition Reactions
paper · doi:10.1126/science.adq3519
openalex publication_date 2024/10/31 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/31
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.