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Mn(OAc)3 catalyzed intermolecular oxidative peroxycyclization of naphthoquinone

Authors :: Christophe Curti
Alex Meye Biyogo
Thierry Terme
Patrice Vanelle
Hussein El-Kashef
Omar Khoumeri
Institut de Chimie Radicalaire (ICR)
Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU)
Assistance Publique - Hôpitaux de Marseille (APHM)
Department of Chemistry
Assiut University
Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Source :: RSC Advances, RSC Advances, Royal Society of Chemistry, 2017, 7 (1), pp.106--111. ⟨10.1039/c6ra25138b⟩, RSC Advances, 2017, 7 (1), pp.106--111. ⟨10.1039/c6ra25138b⟩
Publication Year :: 2017
Publisher :: Royal Society of Chemistry (RSC), 2017.
Abstract: International audience; Manganese(III) acetate-mediated peroxycyclization between 2-hydroxy-3-methylnaphthoquinone and various alkenes was performed to obtain dihydronaphtho[2,3-c][1,2] dioxine-5,10(3H, 10aH)-diones. The reactivity of symmetrical or unsymmetrical 1,1-disubstituted alkenes and monosubstituted alkenes allowed the synthesis of more than 50 original molecules. Focusing on the excellent reactivity of 2-hydroxy-3-methylnaphthoquinone, we describe the first example of Mn(OAc)(3) reactivity with nitro-substituted alkenes. The scope, limitations and stereochemistry of the products synthesized are discussed. Starting from monosubstituted alkenes, the instability of a pair of diastereoisomers was observed, leading to ring opening.