ArticleThe journal of physical chemistry. A2024
Regioselective Rearrangement of Nitrogen- and Carbon-Centered Radical Intermediates in the Hofmann-Löffler-Freytag Reaction.
Article in The journal of physical chemistry. A, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
What it found
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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
3 citing papers in PubMed, 5 citations in OpenAlex.
- Continuous-Wave Electron Paramagnetic Resonance Spectroscopy in Pharmaceutical Research: Current Applications and Emerging Opportunities.Pharmaceuticals (Basel, Switzerland) · 2026Review
- Confined Cationic Covalent Organic Cages Enable Oxidant-Free Hofmann-Löffler-Freytag/Cyclization Sequences.Angewandte Chemie (International ed. in English) · 2026Article
- Mechanistic Insights into the Propagation Cycle of the Hofmann-Löffler-Freytag Reaction: Halogen vs Hydrogen Atom Transfer.The Journal of organic chemistry · 2025Article
Corrections and comments
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Authors and funding
9 authors at 4 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The Hofmann-Löffler-Freytag (HLF) reaction serves as a late-stage functionalization technique for generating pyrrolidine heterocyclic ring systems. Contemporary HLF protocols utilize in situ halogenated sulfonamides as precursors in the radical-mediated rearrangement cycle. Despite its well-established reaction mechanism, experiments toward the detection of radical intermediates using EPR techniques have only recently been attempted. However, the obtained spectra lack the distinct features of the N-centered radicals expected for the employed reactants. This paper presents phenylbutylnitrone spin-trapped C-centered and N-centered radicals, generated via light irradiation from N-halogen-tosyl-sulfonamide derivatives and detected using EPR spectroscopy. NMR spectroscopy and DFT calculations are used to explain the observed regioselectivity of the HLF reaction.
Identifiers
What OpenQuestion holds
Registered trials
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