ArticleJournal of the American Chemical Society2016
Total Synthesis and Characterization of 7-Hypoquinuclidonium Tetrafluoroborate and 7-Hypoquinuclidone BF3 Complex.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Towards the activity of twisted acyclic amides.RSC advances · 2025Article
- Structures of the Most Twisted Thioamide and Selenoamide: Effect of Higher Chalcogens of Twisted Amides on N-C(X) Resonance.Angewandte Chemie (International ed. in English) · 2022Article
- Acyclic Twisted Amides.Chemical reviews · 2021Review
- Total Synthesis of (±)-Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds.Angewandte Chemie (International ed. in English) · 2020Article
- Enhanced reactivity of twisted amides inside a molecular cage.Nature chemistry · 2020Article
- Resonance promoted ring-opening metathesis polymerization of twisted amides.Chemical science · 2019Article
- Amide nitrogen pyramidalization changes lactam amide spinning.Nature communications · 2019Article
- Chemistry of Bridged Lactams: Recent Developments.Molecules (Basel, Switzerland) · 2019Review
- Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation: Application to the Synthesis of Unusual Amino Acids.Journal of the American Chemical Society · 2017Article
- Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A.Angewandte Chemie (International ed. in English) · 2017Article
- Pyramidalization/twisting of the amide functional groupChemical science · 2017Article
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Authors and funding
5 authors.
Funding
Abstract
Derivatives of the fully twisted bicyclic amide 7-hypoquinuclidone are synthesized using a Schmidt-Aubé reaction. Their structures were unambiguously confirmed by X-ray diffraction analysis and extensive spectroscopic characterization. Furthermore, the stability and chemical reactivity of these anti-Bredt amides are investigated. 7-Hypoquinuclidonium tetrafluoroborate is shown to decompose to a unique nitrogen bound amide-BF3 complex of 7-hypoquinuclidone under anhydrous conditions and to react instantaneously with water making it one of the most reactive amides known to date.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.