Photochemically Induced Intramolecular Radical Cyclization Reactions with Imines
| Autor: | Clément Michelin, Corentin Lefebvre, Véronique Bulach, Manabu Abe, Vaneck Djou’ou Mvondo, Thomas Martzel, Norbert Hoffmann |
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| Přispěvatelé: | Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Tectonique Moléculaire du Solide (TMS), Chimie de la matière complexe (CMC), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Department of Chemistry, Graduate School of Science, Hiroshima University (HIRODAI), Hiroshima University |
| Rok vydání: | 2018 |
| Předmět: |
Hydrogen
[CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Diradical Organic Chemistry Imine chemistry.chemical_element Hydrogen atom 010402 general chemistry Hydrogen atom abstraction Photochemistry 01 natural sciences Radical cyclization 0104 chemical sciences chemistry.chemical_compound Intersystem crossing chemistry Intramolecular force |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2018, 83 (4), pp.1867-1875. ⟨10.1021/acs.joc.7b02810⟩ |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.7b02810 |
| Popis: | International audience; The photochemically induced intramolecular hydrogen abstraction or hydrogen atom transfer in cyclic imines 8a,b followed by a cyclization is investigated. Two types of products are observed, one resulting from the formation of a C–C bond, the other from the formation of a C–N bond. A computational study reveals that hydrogen is exclusively transferred to the imine nitrogen leading to a triplet diradical intermediate. After intersystem crossing, the resulting zwitterionic intermediate undergoes cyclization leading to the final product. |
| Databáze: | OpenAIRE |
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