Photochemically Induced Intramolecular Radical Cyclization Reactions with Imines - Université de Reims Champagne-Ardenne Access content directly
Journal Articles Journal of Organic Chemistry Year : 2018

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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hal-02266302 , version 1 (13-08-2019)

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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, 2018, 83 (4), pp.1867-1875. ⟨10.1021/acs.joc.7b02810⟩. ⟨hal-02266302⟩
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