ArticleOrganic letters2017
Mechanistic Duality in Tertiary Amine Additions to Thermally Generated Hexadehydro-Diels-Alder Benzynes.
Article in Organic letters, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- 1The Journal of organic chemistry · 2026Article
- 1,3-Butadiynamides the Ethynylogous Ynamides: Synthesis, Properties and Applications in Heterocyclic Chemistry.Molecules (Basel, Switzerland) · 2023Review
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- Direct observation ofChemical science · 2020Article
- Reactions of HDDA Benzynes withEuropean journal of organic chemistry · 2020Article
- Reactions of thermally generated benzynes with six-memberedChemical science · 2019Article
- Consecutive HDDA and TDDA reactions of silicon-tethered tetraynes for the synthesis of dibenzosilole-fused polycyclic compounds and their unique reactivity.Chemical science · 2019Article
- Reactions of Diaziridines with Benzynes Give N-Arylhydrazones.Organic letters · 2018Article
- Multiheterocyclic Motifs via Three-Component Reactions of Benzynes, Cyclic Amines, and Protic Nucleophiles.Organic letters · 2018Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Reported here are studies directed at understanding the mechanism of tertiary amine addition to hexadehydro-Diels-Alder (HDDA)-generated benzynes. Tertiary amines are presumed to engage benzynes by generation of a zwitterionic intermediate. Simple trialkylamines undergo intermolecular protonation by a protic nucleophile to give an aryl ammonium intermediate that is then dealkylated. Amines containing acidified β-protons undergo an intramolecular elimination to give the aniline and an alkene. Finally, amino alcohols react at either of their N- or O atoms, depending upon the extent of internal hydrogen bonding.
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