ArticleChemical science2024
Mild and catalytic electrocyclizations of heptatrienyl anions.
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 2 papers.
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Who cites it
2 citing papers in PubMed.
- Alkali-Metal Base Catalyzed Electrocyclization of Isoprene Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Computational Study of Ignored Pericyclic Reactions: Rearrangements of 1,2-Bis(Diazo)Alkanes to 1,2,3,4-Tetrazines and Subsequent Fragmentations.Angewandte Chemie (International ed. in English) · 2025Article
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Authors and funding
8 authors.
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Abstract
We report the synthesis of functionalized cycloheptanes by thermal electrocyclization of heptatrienyl anions under mild conditions. In addition, we disclose the first examples of this electrocyclization manifold conducted under catalytic conditions. Previously, electrocyclization of heptatrienyl systems required formation of anions with a strong base, resulting in limited functional group compatibility. We demonstrate that polarization of heptatrienyl anions using strategically positioned electron-withdrawing groups lowers the energy landscape of the reaction by stabilizing both the acyclic heptatrienyl anion and cycloheptadienyl product. Divergent reactivity is observed between aliphatic and aromatic substrates, with the latter requiring only catalytic amounts of base for complete conversion. This can be rationalized by the relative stability of the acyclic and cyclic anions and their ability to participate in a chain reaction process.
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