ArticleNature communications2018
Differentiation between enamines and tautomerizable imines in the oxidation reaction with TEMPO.
Article in Nature communications, 2018. 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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Who cites it
10 citing papers in PubMed.
- Rotational observation of kinetically hindered neutral radical pairs.Nature communications · 2026Article
- Precise control of selective nitrogen atom insertion into five-membered cyclic β-ketoesters.Nature communications · 2025Article
- Interception and Synthetic Application of Diradical and Diene Forms of Dual-Nature Azabicyclic o-Quinodimethanes Generated by 6π-Azaelectrocyclization.Angewandte Chemie (International ed. in English) · 2024Article
- Tandem dehydrogenation-olefination-decarboxylation of cycloalkyl carboxylic acids via multifold C-H activation.Nature communications · 2024Article
- Dehydrogenative synthesis ofScience advances · 2024Article
- Article
- Interception of 1,2-cyclohexadiene with TEMPO radical.Tetrahedron letters · 2021Article
- Metal-free C(spChemical science · 2021Article
- Copper-catalyzed dehydrogenative γ-C(spNature communications · 2019Article
- Differentiation between Enamines and Tautomerizable Imines Oxidation Reaction Mechanism using Electron-Vibration-Vibration Two Dimensional Infrared Spectroscopy.Molecules (Basel, Switzerland) · 2019Article
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Enamine and imine represent two of the most common reaction intermediates in syntheses, and the imine intermediates containing α-hydrogen often exhibit the similar reactivity to enamines due to their rapid tautomerization to enamine tautomers. Herein, we report that the minor structural difference between the enamine and the enamine tautomer derived from imine tautomerization results in the different chemo- and regioselectivity in the reaction of cyclohexanones, amines and TEMPO: the reaction of primary amines furnishes the formal oxygen 1,2-migration product, α-amino-enones, while the reaction of secondary amines under similar conditions generates exclusively arylamines via consecutive dehydrogenation on the cyclohexyl rings. The
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