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- W2950371423 abstract "A Nef reaction has been developed that is conducted under mildly basic conditions with molecular oxygen as an oxidant, without the need for metal additives. Whereas nitroalkanes are converted into ketones in good yield, nitroalkenes are transformed into α,β-unsaturated ketones in one-pot by double-bond isomerization followed by the oxygen-mediated Nef reaction. The reaction protocol is both mild and general, and tolerates acid- and base-labile functionality or protecting groups. When oxygen-saturated solvents are employed, the reaction completes within 20 min. Mechanistically, the addition of nitronate ion and molecular oxygen is proposed to proceed initially through a single-electron transfer event, as indicated by radical clock experiments. This ultimately generates a putative 1,1-dioxirane, which reacts further with another nitronate ion to generate the ketone. Involvement of a 1,1-dioxirane is supported by intramolecular trapping experiments with sulfide at the γ-position of the nitro-moiety." @default.
- W2950371423 created "2019-06-27" @default.
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- W2950371423 date "2015-04-01" @default.
- W2950371423 modified "2023-09-27" @default.
- W2950371423 title "ChemInform Abstract: Nef Reaction with Molecular Oxygen in the Absence of Metal Additives, and Mechanistic Insights." @default.
- W2950371423 cites W2108893251 @default.
- W2950371423 doi "https://doi.org/10.1002/chin.201517073" @default.
- W2950371423 hasPublicationYear "2015" @default.
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