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Novel access to verbenone via ruthenium nanoparticles-catalyzed oxidation of Α-pinene in neat water

Abstract : Aqueous suspensions of Ru(0) nanoparticles, stabilized with hydroxyethylammonium salts and possessing sizes around 2 nm, proved to be active and selective in the mild oxidation of α-pinene in the presence of tert-butylhydroperoxide, in neat water. Verbenone, a product of great interest for fine chemistry, was obtained as major product with yield up to 41% under optimized conditions. 2-hydroxy-3-pinanone was identified as a co-product of the reaction, but with very low amount (<7%). Kinetic investigations allowed determining the potential reaction intermediates and by-products. Moreover, mechanistic studies with radical scavengers confirmed that α-pinene oxidation mainly implies both carbon- and oxygen-centered radicals. © 2017 Elsevier B.V.
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Submitted on : Wednesday, February 28, 2018 - 3:15:49 PM
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M. Rauchdi, M. Ait Ali, A. Roucoux, A. Denicourt-Nowicki. Novel access to verbenone via ruthenium nanoparticles-catalyzed oxidation of Α-pinene in neat water. Applied Catalysis A : General, Elsevier, 2018, 550, pp.266-273. ⟨10.1016/j.apcata.2017.11.016⟩. ⟨hal-01671613⟩

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