ArticleChemical science2024
Cascade reactions of HDDA-benzynes with tethered cyclohexadienones: strain-driven events originating from
Article in Chemical science, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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Who cites it
1 citing paper in PubMed.
- Cyclic Osmate Esters from 1,2- and 1,3-Diols and α-Hydroxy Acids for X-ray Analysis.The Journal of organic chemistry · 2025Article
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Authors and funding
3 authors.
Funding
Abstract
Intramolecular net [2 + 2] cycloadditions between benzyne intermediates and an electron-deficient alkene to give benzocyclobutene intermediates are relatively rare. Benzynes are electrophilic and generally engage nucleophiles or electron-rich π-systems. We describe here reactions in which an alkene of a tethered enone traps thermally generated benzynes in a variety of interesting ways. The number of atoms that link the benzyne to C4 of a cyclohexa-2,5-dienone induces varying amounts of strain in the intermediates and products. This leads to a variety of different reaction outcomes by way of various strain-releasing events that are mechanistically intriguing. This work demonstrates an underappreciated class of strain that originates from the adjacent fusion of two rings to both C1-C2 and C2-C3 of a benzenoid ring -
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Registered trials
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