ArticleThe Journal of organic chemistry2026
Spiro-Induced Strain as a Design Principle for Long-Lived Singlet Diradicals with π-Single Bond Character.
Article in The Journal of organic chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Singlet 1,3-diradicals with a π single-bond character exhibit unique electronic structures and attractive photophysical and redox properties; however, their practical utilization is severely limited by rapid σ-bond formation and competing rearrangement pathways. Here, we demonstrate that spiro-induced strain provides a design principle for controlling competing reaction pathways in singlet diradicals. Quantum chemical calculations using CASSCF and broken-symmetry DFT methods reveal that this strain destabilizes both σ-bonded products and the corresponding transition states, thereby suppressing σ-bond formation. This effect is most pronounced for a spirocyclic system
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