ArticleJournal of the American Chemical Society2017
Computational Exploration of Concerted and Zwitterionic Mechanisms of Diels-Alder Reactions between 1,2,3-Triazines and Enamines and Acceleration by Hydrogen-Bonding Solvents.
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 10 papers.
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10 citing papers in PubMed, 46 citations in OpenAlex.
- Denitrogenative dismantling of heteroaromatics by nucleophilic substitution reactions with diazomethyl compounds.Chemical science · 2024Article
- Site Reversal in Nucleophilic Addition to 1,2,3-Triazine 1-Oxides.Journal of the American Chemical Society · 2023Article
- Acyclic and Heterocyclic Azadiene Diels-Alder Reactions Promoted by Perfluoroalcohol Solvent Hydrogen Bonding: Comprehensive Examination of Scope.The Journal of organic chemistry · 2022Article
- Understanding chemistry: from "heuristic (soft) explanations and reasoning by analogy" to "quantum chemistry".Chemical science · 2022Review
- Mechanistic Insights into the Reaction of Amidines with 1,2,3-Triazines and 1,2,3,5-Tetrazines.Journal of the American Chemical Society · 2022Article
- Electric field-catalyzed single-molecule Diels-Alder reaction dynamics.Science advances · 2021Article
- Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding.Journal of the American Chemical Society · 2020Article
- Silylium ion mediated 2+2 cycloaddition leads to 4+2 Diels-Alder reaction products.Communications chemistry · 2020Article
- Synthesis, Characterization, and Cycloaddition Reactivity of a Monocyclic Aromatic 1,2,3,5-Tetrazine.Journal of the American Chemical Society · 2019Article
- Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes - a reaction at the 'oxonium-Prins'Chemical science · 2019Article
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3 authors at 1 institution in 1 country.
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Abstract
The mechanisms of Diels-Alder reactions between 1,2,3-triazines and enamines have been explored with density functional theory computations. The focus of this work is on the origins of the different reactivities and mechanisms induced by substituents and by hexafluoroisopropanol (HFIP) solvent. These inverse electron-demand Diels-Alder reactions of triazines have wide applications in bioorthogonal chemistry and natural product synthesis. Both concerted and stepwise cycloadditions are predicted, depending on the nature of substituents and solvents. The nature of zwitterionic intermediates and the mechanism by which HFIP accelerates cycloadditions with enamines are characterized. Our results show the delicate nature of the concerted versus stepwise mechanism of inverse electron-demand Diels-Alder reactions of 1,2,3-triazines, and that these mechanisms can be altered by electron-withdrawing substituents and hydrogen-bonding solvents.
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