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Mn(OAc)(3) catalyzed intermolecular oxidative peroxycyclization of naphthoquinone

Abstract : 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.
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https://hal-amu.archives-ouvertes.fr/hal-01774203
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Submitted on : Monday, April 23, 2018 - 2:42:25 PM
Last modification on : Wednesday, August 19, 2020 - 12:08:20 PM

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Alex Meye Biyogo, Christophe Curti, Hussein El-Kashef, Omar Khoumeri, Thierry Terme, et al.. Mn(OAc)(3) catalyzed intermolecular oxidative peroxycyclization of naphthoquinone. RSC Advances, Royal Society of Chemistry, 2017, 7 (1), pp.106--111. ⟨10.1039/c6ra25138b⟩. ⟨hal-01774203⟩

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