26218-72-4Relevant articles and documents
Oxidation of: O -dioxime by (diacetoxyiodo)benzene: Green and mild access to furoxans
He, Chunlin,Pang, Siping,Zhang, Qi,Zhang, Xun,Zhao, Cheng
supporting information, p. 1489 - 1493 (2022/01/31)
Furoxan has been widely used in the field of high energy density materials because of its excellent properties such as high density, high standard enthalpy of formation and high nitrogen content. However, its existing synthesis methods are still restricted by the problems of difficult substrate preparation and manual handling of hazardous reagents. Herein, we disclosed a mild oxidation strategy to efficiently obtain furoxan derivatives starting from readily available o-dioxime substrates. This reaction features high functional group tolerance and easy scale-up, and has excellent regioselectivity for specific nonsymmetric o-dioximes. This method greatly reduces the safety risk and simplifies the operation process, and means that diversified furoxan derivatives can be easily accessed, thus paving the way for the wide application of furoxan derivatives. This journal is
Efficient synthesis of isoxazoles and isoxazolines from aldoximes using Magtrieve (CrO2)
Bhosale, Sandeep,Kurhade, Santosh,Prasad, Uppuleti Viplava,Palle, Venkata P.,Bhuniya, Debnath
scheme or table, p. 3948 - 3951 (2009/10/11)
Treatment of aldoximes 1 with Magtrieve (CrO2) in presence of dipolarophile 3 or 4, furnished a variety of isoxazolines 5a-u and isoxazoles 6a-q as 1,3-dipolar cycloaddition (1,3-DC) products (38 examples; 63-90% isolated yields). In situ formation of a nitrile oxide intermediate was confirmed through isolation of the dimerization product furoxane 2a in absence of any dipolarophile. The methodology has been extended to intramolecular nitrile oxide cycloaddition (INOC) reactions to access highly useful chromane derivatives 7-8 (75-80% isolated yields). Magtrieve, as a new reagent for 1,3-DC reactions, has offered excellent substrate generality and at the same time demonstrated tolerance toward sensitive protecting groups and electron-rich functional groups.
Cycloadditions of Nitrile Oxides and Nitrones to 4,4-Methylene-1-methylpiperidine: Studies in Regio- and Stereoselectivity
Fisera, L.,Sauter, F.,Froehlich, J.,Feng, Y.,Ertl, P.,Mereiter, K.
, p. 553 - 564 (2007/10/02)
A series of spiro-substituted isoxazole derivatives were synthesized by 1,3-dipolar cycloadditions of nitrile oxides and nitrones to 4,4-methylene-1-methylpiperidine.Since nmr studies confirmed that only one regioisomer was formed selectively, semi-empirical quantum mechanical methods (AM1) were used to rationalize this regiochemical preference via calculation and inspection of HOMO-LUMO-energy and coefficients.X-ray structure analysis carried out for one of these products showed the occurrence of only one stereoisomer, explicable by comparing AM1-calculated ΔHf-values of all possible cycloadducts. - Keywords: 1,3-Dipolar cycloaddition; Nitrile oxide; Nitrone; 4,4-Methylene-1-methylpiperidine; AM1 calculations.