ArticleJournal of physical organic chemistry2023
Spirocyclization enhances the Diels-Alder reactivities of geminally substituted cyclopentadienes and 4
Article in Journal of physical organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
3 citing papers in PubMed.
- Taming the 1,5-sigmatropic shift across protonated spirocyclic 4Journal of physical organic chemistry · 2024Article
- Computational study of an oxetane 4Tetrahedron letters · 2023Article
- Bioorthogonal 4Chemical communications (Cambridge, England) · 2023Article
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Authors and funding
3 authors.
Funding
Abstract
The Diels-Alder reactivity of 5-membered dienes is tunable through spirocyclization at the saturated center. As the size of the spirocycle decreases, the Diels-Alder reactivity increases with the cyclobutane spirocycle, spiro[3.4]octa-5,7-diene, being the most reactive. Density functional theory calculations suggest that spiro[3.4]octa-5,7-diene dimerizes 220,000-fold faster than 5,5-dimethylcyclopentadiene and undergoes a Diels-Alder reaction with ethylene 1,200-fold faster than 5,5-dimethylcyclopentadiene. These findings show that spirocyclization is an effective way to enhance the Diels-Alder reactivity of geminally substituted 5-membered dienes.
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Registered trials
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