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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
1 ICMR - Institut de Chimie Moléculaire de Reims - UMR 7312
2 TMS - Tectonique Moléculaire du Solide
CMC - Chimie de la matière complexe
3 HIRODAI - Department of Chemistry, Graduate School of Science, Hiroshima University
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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https://hal.univ-reims.fr/hal-02266302
Contributor : Norbert Hoffmann Connect in order to contact the contributor
Submitted on : Tuesday, August 13, 2019 - 8:33:01 PM
Last modification on : Wednesday, November 3, 2021 - 6:54:53 AM

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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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