5050-65-7Relevant articles and documents
Generation of Iminoxyl Radicals by Photoredox Catalysis Enables Oxidant-Free Hydroxygenation of β,γ-Unsaturated Oximes
Chen, Huiming,Li, Zhenming,Qian, Lijie,Xu, Xiangsheng
supporting information, p. 293 - 295 (2021/11/30)
A visible-light photocatalytic generation of iminoxyl radicals has been accomplished under oxidant-free conditions. This approach offers a mild, atom-economical, and redox-neutral synthesis of 5-methylisoxazolines through radical hydroxygenation of β,γ-unsaturated oximes in the absence of an additional hydrogen source.
Study of the Features of the Reaction of Arylcyclopropanes with Nitrozonium Ethyl Sulfate or Nitrozonium Tetrafluoroborate
Bondarenko, O. B.,Gavrilova, A. Yu.,Solodovnikova, T. A.,Tikhanushkina, V. N.,Zyk, N. V.
, p. 753 - 762 (2020/07/03)
Abstract: The reactions of diaryl-, aryl-, and alkyl–arylcyclopropanes with ethyl nitrite in the presence of sulfur trioxide and sulfur trioxide dioxane complex, as well as the reactions of 1-alkyl-2-arylcyclopropanes with NOBF4 were studied. It was found that the attack of the nitrosonium cation, accompanied by the formation of a benzyl carbocation, leads to the formation of isoxazolines. The introduction of bulky alkyl substituents into the cyclopropane ring changes the regioselectivity of nitrosation, favoring the attack of the electrophilic particle on the benzyl position and leading to the competitive formation of an alkyl carbocation. Depending on the structure of the alkyl substituent, both products of intramolecular heterocyclization accompanied by skeletal rearrangements and products formed with the participation of an external nucleophile are formed.
A tandem oximation-cyclization route to Δ2-isoxazolines
Norman, Amber L.,Shurrush, Khriesto A.,Calleroz, Amanda T.,Mosher, Michael D.
, p. 6849 - 6851 (2008/02/12)
3,5-Disubstituted Δ2-isoxazolines can be prepared from the corresponding β,γ-unsaturated ketones by treatment with hydroxylamine hydrochloride and sodium hydroxide. Evidence indicates that the mechanism of this reaction involves the formation o