51003-63-5Relevant academic research and scientific papers
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.
New methods of preparation of nitrile oxides and the corresponding disubstituted furoxans by interaction of N2O4 with salts of substituted dinitromethanes
Makhova, N. N.,Ovchinnikov, I. V.,Dubonos, V. G.,Strelenko, Yu. A.,Khmel'nitsky, L. I.
, p. 131 - 136 (2007/10/02)
A new method of generation of nitrile oxides through interaction of N2O4 with salts of substituted dinitromethanes (1) has been worked out.It has been shown by 1H, 13C, 14N NMR spectroscopy that this reaction proceeds via dinitrosomethyl intermediates (on
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.
SYNTHESES BASED ON NITRILE OXIDES. 1. REACTION OF AROMATIC NITRILE OXIDES WITH N-CYANAMIDES
Ogurtsov, V. A.,Rakitin, O. A.,Obruchnikova, N. V.,Chertanova, L. F.,Gazikasheva, A. A.,Khmel'nitskii, L. T.
, p. 1896 - 1900 (2007/10/02)
The reaction of trialkylaminocyanimides with aromatic nitrile oxides leads to trialkylamino-(3-aryl-1,2,4-oxadiazol-5-yl)imides, while the corresponding reactions with sulfylcyanimines and phosphincyanimides do not take place.Using x-ray structural analysis the principal structural features of the 1,2,4-oxadiazole products have been elucidated.
