ArticleJournal of the American Chemical Society2016
Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.
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 23 papers.
What it found
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Who cites it
23 citing papers in PubMed.
- Tandem cyclohexen-3-yne and 1,2,3-cyclohexatriene reactions.Nature communications · 2026Article
- Mechanisms of Kobayashi eliminations for the generation of highly strained arynes, cyclic cumulenes, and anti-Bredt olefins.Chemical science · 2025Article
- Synthesis and reactivity of nitrogen-containing strained cyclic 1,2,3-trienes.Nature synthesis · 2025Article
- Skeletal Rearrangements of Amides via Breaking Inert Bonds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Formation of 3-Oxa- and 3-Thiacyclohexyne from Ring Expansion of Heterocyclic Alkylidene Carbenes: A Mechanistic Study.Organic letters · 2023Article
- Cycloaddition Cascades of Strained Alkynes and Oxadiazinones.Angewandte Chemie (International ed. in English) · 2021Article
- Review
- Palladium-Catalyzed Annulations of Strained Cyclic Allenes.Journal of the American Chemical Society · 2021Article
- Article
- Coumarin (5,6-Benzo-2-pyrone) Trapping of an HDDA-Benzyne.Organic letters · 2021Article
- Silyl Tosylate Precursors to Cyclohexyne, 1,2-Cyclohexadiene, and 1,2-Cycloheptadiene.Organic letters · 2020Article
- Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds.Angewandte Chemie (International ed. in English) · 2019Article
- Cycloadditions of Oxacyclic Allenes and a Catalytic Asymmetric Entryway to Enantioenriched Cyclic Allenes.Angewandte Chemie (International ed. in English) · 2019Article
- Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors.The Journal of organic chemistry · 2019Article
- Ring Expansion of Alkylidenecarbenes Derived from Lactams, Lactones, and Thiolactones into Strained Heterocyclic Alkynes: A Theoretical Study.Molecules (Basel, Switzerland) · 2019Article
- Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.Journal of the American Chemical Society · 2019Article
- Transition-Metal-Free Activation of Amide Bond by Arynes.Molecules (Basel, Switzerland) · 2018Review
- Arynes and Cyclic Alkynes as Synthetic Building Blocks for Stereodefined Quaternary Centers.Journal of the American Chemical Society · 2018Article
- [3 + 2]-Cycloaddition reaction of sydnones with alkynes.Beilstein journal of organic chemistry · 2018Review
- Synthesis and Utilization of Nitroalkyne Equivalents in Batch and Continuous Flow.Angewandte Chemie (International ed. in English) · 2017Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
We report synthetic methodology that permits access to two oxacyclic strained intermediates, the 4,5-benzofuranyne and the 3,4-oxacyclohexyne. In situ trapping of these intermediates affords an array of heterocyclic scaffolds by the formation of one or more new C-C or C-heteroatom bonds. Experimentally determined regioselectivities were consistent with predictions made using the distortion/interaction model and were also found to be greater compared to selectivities seen in the case of trapping experiments of the corresponding N-containing intermediates. These studies demonstrate the synthetic versatility of oxacyclic arynes and alkynes for the synthesis of functionalized heterocycles, while further expanding the scope of the distortion/interaction model. Moreover, these efforts underscore the value of harnessing strained heterocyclic intermediates as a unique approach to building polycyclic heteroatom-containing frameworks.
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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.