ArticleAngewandte Chemie (International ed. in English)2018
Benzocyclobutadienes: An Unusual Mode of Access Reveals Unusual Modes of Reactivity.
Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
11 citing papers in PubMed.
- Rh-Catalyzed in Situ Generation of Phenanthrocyclobutadienes from Tetraaryl-Diynes and Their Cycloadditions with Cycloalkenediones andOrganic letters · 2025Article
- A Distinct Mode of Strain-Driven Cyclic Allene Reactivity: Group Migration to the Central Allene Carbon Atom.Journal of the American Chemical Society · 2023Article
- Electronic Character of α,3-Dehydrotoluene Intermediates Generated from Isolable Allenyne-Containing Substrates.Angewandte Chemie (International ed. in English) · 2022Article
- Silicon as a powerful control element in HDDA chemistry: redirection of innate cyclization preferences, functionalizable tethers, and formal bimolecular HDDA reactions.Chemical science · 2021Article
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- Highly Conjugated π-Systems Arising from Cannibalistic Hexadehydro-Diels-Alder Couplings: Cleavage of C-C Single and Triple Bonds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Direct observation ofChemical science · 2020Article
- One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents.Journal of the American Chemical Society · 2019Article
- Benzyne Cascade Reactions via Benzoxetenonium Ions and Their Rearrangements to o-Quinone Methides.Organic letters · 2019Article
- CuAngewandte Chemie (International ed. in English) · 2018Article
- BFJournal of the American Chemical Society · 2018Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
The reaction of an aryne with an alkyne to generate a benzocyclobutadiene (BCB) intermediate is rare. We report here examples of this reaction, revealed by Diels-Alder trapping of the BCB by either pendant or external electron-deficient alkynes. Mechanistic delineation of the reaction course is supported by DFT calculations. A three-component process joining the benzyne first with an electron-rich and then with an electron-poor alkyne was uncovered. Reactions in which the BCB functions in a rarely observed role as a 4π diene component in Diels-Alder reactions are reported. The results also shed new light on aspects of the hexadehydro-Diels-Alder reaction used to generate the benzynes.
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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.