ArticleJournal of the American Chemical Society2017
Photochemical Hexadehydro-Diels-Alder Reaction.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Rh-Catalyzed [2 + 2 + 2] Cycloaddition of Linked Bis(Diynes) Ar-C≡C-C≡C-(CHChemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Cycloadditions of Benzynes with the Azoxy [RN═NOrganic letters · 2024Article
- The contrasting reactivity ofChemical science · 2023Article
- A symmetry-driven approach toward the total synthesis of dodecahedrane.Tetrahedron · 2022Article
- DNA Walkers for Biosensing Development.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2022Review
- Radial hexadehydro-Diels-Alder reactions.Chem · 2021Article
- Cu(I)-Catalyzed 1,2-Alkynyl-propargylation and -benzylation of Benzyne Derivatives.Organic letters · 2021Article
- Mechanistic and Kinetic Factors of ortho-Benzyne Formation in Hexadehydro-Diels-Alder (HDDA) Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Diazocarbonyl and Related Compounds in the Synthesis of Azoles.Molecules (Basel, Switzerland) · 2021Review
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- Diels-Alder Cycloaddition to the Bay Region of Perylene and Its Derivatives as an Attractive Strategy for PAH Core Expansion: Theoretical and Practical Aspects.Molecules (Basel, Switzerland) · 2020Review
- Direct observation ofChemical science · 2020Article
- Conceptual similarities between zeolites and artificial enzymes.Chemical science · 2019Article
- Reactions of Diaziridines with Benzynes Give N-Arylhydrazones.Organic letters · 2018Article
- A Traceless Tether Strategy for Achieving Formal Intermolecular Hexadehydro-Diels-Alder Reactions.Organic letters · 2018Article
- The domino hexadehydro-Diels-Alder reaction transforms polyynes to benzynes to naphthynes to anthracynes to tetracynes (and beyond?).Nature chemistry · 2018Article
- Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C(spChemical science · 2018Article
- Mechanistic Duality in Tertiary Amine Additions to Thermally Generated Hexadehydro-Diels-Alder Benzynes.Organic letters · 2017Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
We demonstrate that the hexadehydro-Diels-Alder (HDDA) cycloisomerization reaction to produce reactive benzyne derivatives can be initiated photochemically. As with the thermal variant of the HDDA process, the reactive intermediates are formed in the absence of reagents or the resulting byproducts required for the generation of benzynes by traditional methods. This photo-HDDA (or hν-HDDA) reaction occurs at much lower temperatures (including even at -70 °C) than the thermal HDDA, but the benzynes produced behave in the same fashion with respect to their trapping reactions, suggesting they are of the same electronic state.
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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.