51003-63-5Relevant articles and documents
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.
Regioselective synthesis of C-nucleosides by 1,3-dipolar cycloaddition of arylnitrile oxides to 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose
Al-Timari, Usama A. R.,Fisera, Lubor
, p. 121 - 127 (2007/10/02)
The synthesis of 3-aryl-5-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-2-isoxazoline (3) from arylnitrile oxides and 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (1) is described.The 1,3-dipolar cycloaddition reactions give mainly anti-adducts (>=95percent ?-facial stereoselectivity).
REACTIONS OF NITRILE OXIDES WITH NITROGEN OXIDES. 2. REACTIONS WITH NITROGEN MONOXIDE AND NITROGEN SESQUIOXIDE
Rakitin, O. A.,Ogurtsov, V. A.,Godovikova, T. I.,Khmel'nitskii, L. I.
, p. 1472 - 1474 (2007/10/02)
We have studied the reactions of aromatic nitrile oxides with nitrogen monoxide and nitrogen sesquioxide.It was shown that the nitrogen monoxide removes an oxygen atom from the nitrile oxide with formation of the corresponding nitrile and nitrogen dioxide.The reaction products with nitrogen sesquioxide are formed as a result of reactions of the nitrile oxide with nitrogen monoxide and nitrogen tetroxide.