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Journal articles
Photochemically Induced Intramolecular Radical Cyclization Reactions with Imines
Corentin Lefebvre
1
Clement Michelin
1
Thomas Martzel
1
Vaneck Djou’ou Mvondo
1
Véronique Bulach
2
Manabu Abe
3
Norbert Hoffmann
1
Corentin Lefebvre 1
Author
Clement Michelin 1
Author
Thomas Martzel 1
Author
Vaneck Djou’ou Mvondo 1
Author
Véronique Bulach 2
Author
Manabu Abe 3
Author
Norbert Hoffmann 1
Mail :
Author Employer institution : Université de Reims Champagne-Ardenne
1
ICMR - Institut de Chimie Moléculaire de Reims - UMR 7312 (UFR Sciences, BP1039, 51687 Reims Cedex 2 - France)
- SFR Condorcet (France)
- URCA - Université de Reims Champagne-Ardenne : CNRS 3417 (9 boulevard de la Paix - CS 60005 - 51724 Reims cedex - France)
- UPJV - Université de Picardie Jules Verne : CNRS 3417 (Chemin du Thil - 80000 Amiens - France)
- CNRS - Centre National de la Recherche Scientifique : CNRS 3417 (France)
- SFR CAP Santé (Champagne-Ardenne Picardie Santé) (Faculté de Médecine de Reims, 51, rue Cognacq Jay, CS 30018,
51095 Reims Cedex - France)
- URCA - Université de Reims Champagne-Ardenne : FED 4231 (9 boulevard de la Paix - CS 60005 - 51724 Reims cedex - France)
- UPJV - Université de Picardie Jules Verne : FED 4231 (Chemin du Thil - 80000 Amiens - France)
- URCA - Université de Reims Champagne-Ardenne : UMR7312 (9 boulevard de la Paix - CS 60005 - 51724 Reims cedex - France)
- CNRS - Centre National de la Recherche Scientifique : UMR7312 (France)
2
TMS - Tectonique Moléculaire du Solide (Institut Le Bel 4, rue Blaise Pascal 67070 STRASBOURG CEDEX - France)
- CMC - Chimie de la matière complexe (Université de Strasbourg - Institut Le Bel - 4, rue Blaise Pascal - 67070 STRASBOURG CEDEX - France)
- UNISTRA - Université de Strasbourg (4 rue Blaise Pascal - CS 90032 - 67081 Strasbourg cedex - France)
- CNRS - Centre National de la Recherche Scientifique : UMR7140 (France)
3
HIRODAI - Department of Chemistry, Graduate School of Science, Hiroshima University (1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan - Japan)
- Hiroshima University (Japan)
Abstract : 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.
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Journal articles
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Complete list of metadatas
https://hal.univ-reims.fr/hal-02266302
Contributor : Norbert Hoffmann <>
Submitted on : Tuesday, August 13, 2019 - 8:33:01 PM
Last modification on : Wednesday, May 6, 2020 - 1:01:24 AM
Contributor : Norbert Hoffmann <>
Submitted on : Tuesday, August 13, 2019 - 8:33:01 PM
Last modification on : Wednesday, May 6, 2020 - 1:01:24 AM
Identifiers
- HAL Id : hal-02266302, version 1
- DOI : 10.1021/acs.joc.7b02810
Collections
URCA | CNRS | INC-CNRS | ICMR | SITE-ALSACE
Citation
Corentin Lefebvre, Clement Michelin, Thomas Martzel, Vaneck Djou’ou Mvondo, Véronique Bulach, et al.. Photochemically Induced Intramolecular Radical Cyclization Reactions with Imines. Journal of Organic Chemistry, American Chemical Society, 2018, 83 (4), pp.1867-1875. ⟨10.1021/acs.joc.7b02810⟩. ⟨hal-02266302⟩
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