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HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin
Published on: July 23, 2016
Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition
Yulia V Khoroshunova1,2, Denis A Morozov1,2, Andrey I Taratayko1,2
1N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Academician Lavrentiev Ave. 9, Novosibirsk 630090, Russian Federation.
Abstract:
Sterically shielded nitroxides of the pyrrolidine series have shown the highest resistance to reduction. Here we report the synthesis of new pyrrolidine nitroxides from 5,5-dialkyl-1-pyrroline N-oxides via the introduction of a pent-4-enyl group to the nitrone carbon followed by an intramolecular 1,3-dipolar cycloaddition reaction and isoxazolidine ring opening. The kinetics of reduction of the new nitroxides with ascorbate were studied and compared to those of previously published (1S,2R,3'S,4'S,5'S,2″R)-dispiro[(2-hydroxymethyl)cyclopentan-1,2'-(3',4'-di-tert-butoxy)pyrrolidine-5',1″-(2″-hydroxymethyl)cyclopentane]-1'-oxyl (1).
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