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Photochemically Induced Intramolecular Radical Cyclization Reactions with Imines

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 <>
Submitted on : Tuesday, August 13, 2019 - 8:33:01 PM
Last modification on : Wednesday, May 6, 2020 - 1:01:24 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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