7064-07-5Relevant academic research and scientific papers
Nitrile oxide 1,3-dipolar cycloaddition by dehydration of nitromethane derivatives under continuous flow conditions
Brasholz, Malte,Saubern, Simon,Savage, G. Paul
experimental part, p. 1397 - 1401 (2012/02/01)
Aliphatic nitrile oxides were generated in situ, by dehydration of terminal nitro compounds, and reacted with dipolarophiles using continuous flow techniques to afford substituted isoxazolines. The yields of cycloadducts were comparable with traditional f
An expeditious synthesis of isoxazoline using cetyltrimethylammonium cerium nitrate: A phase transferring oxidative 1,3-dipolar cycloaddition
Kumar, Parvin,Kumar, Ashwani
experimental part, p. 1287 - 1290 (2011/10/05)
An expeditious and effective method for synthesis of isoxazoline from aldoximes and activated alkenes using cetyltrimethylammonium cerium nitrate at room temperature is described. Reaction was completed within short time period in high yields at room temp
Magtrieve (CrO2) and MnO2 mediated oxidation of aldoximes: Studying the reaction course
Bhosale, Sandeep,Kurhade, Santosh,Vyas, Samir,Palle, Venkata P.,Bhuniya, Debnath
scheme or table, p. 9582 - 9588 (2011/01/03)
Magtrieve (CrO2) and MnO2 mediated oxidation of aldoximes to nitrile oxides were studied in details. In presence of external radical source, TEMPO, these reagents did not furnish nitrile oxides, instead favoured deoximation to aldehydes. A common trend of deoximation was established from electronically tuned aldoximes, which is: aliphatic>aromatic> aldoximes with strong electron-withdrawing group, though the extent of deoximation was less in case of CrO2. Above effects were not observed with chloramine-T and diacetoxyiodobenzene, reagents known to produce nitrile oxides via hydroximoyl halide or equivalent ionic intermediates. A putative reaction mechanism is proposed for MO2 (M=Cr, Mn) mediated oxidation of aldoximes through formation of a nitroso-oxime tautomeric pair. Formation of nitrile oxide is possibly occurred from the oxime tautomer via a σ-type iminoxy radical intermediate. The deoximation process, dominating in presence of external radical environment, is explained following decomposition of the nitroso tautomer.
New method of in situ generation of nitrile oxides by MnO2 oxidation of aldoximes
Kiegiel, Jaroslaw,Poplawska, Magdalena,Jozwik, Julita,Kosior, Malgorzata,Jurczak, Janusz
, p. 5605 - 5608 (2007/10/03)
Manganese(IV) oxide (MnO2) was found to oxidize aldoximes to nitrile oxides. Nitrile oxides were trapped in situ with dipolarophiles to furnish 2- oxazolines. The best results were obtained with hydroximinoacetates as nitrile oxide precursors.
Generation of nitrile oxides from oxime derivatives by the oxidation with ammonium hexanitratocerate(IV)
Arai, Noriyoshi,Iwakoshi, Mitsuhiko,Tanabe, Katsuhiko,Narasaka, Koichi
, p. 2277 - 2285 (2007/10/03)
Aromatic and aliphatic nitrile oxides are generated by the oxidation of α-hydroxyimino carboxylic acid with ammonium hexanitratocerate(IV). They react with olefinic and acetylenic dipolarophiles to give the corresponding cycloaddition products in good yield. The oxidation of α-oxo aldoximes also affords α-oxo carbonitrile oxides.
A new route to nitrile oxides from primary alkylhalides for in situ dipolar cycloadditions
Maiti, Dilipkumar,Bhattacharya, Pranab K.
, p. 385 - 386 (2007/10/03)
A new route to nitrile oxide preparation from primary alkylbromide, chloride, nitrite and their cycloadditions with olefins to form isoxazolines in a single pot are described.
Intermodular 1,3-dipolar cycloaddition of nitrite oxides with vinyl acetate and acrylonitrile
Lokanatha Rai,Hassner, Alfred
, p. 242 - 245 (2007/10/03)
Reaction of several nitrile oxides 2, isolated from the oxidative dehydrogenation of aldoximes by chloramine-T, with vinyl acetate and acrylonitrile proceeds in better yield than if the nitrile oxides are generated in situ. Solvent effects are also consid
An improved method for preparation of nitrile oxides from nitroalkanes for in situ dipolar cycloadditions
Basel, Yochai,Hassner, Alfred
, p. 309 - 312 (2007/10/03)
A new method has been found for generation of nitrile oxides in situ from nitroalkanes under mild conditions. Thus, reaction of nitroalkanes 1 with di-tert-butyl dicarbonate (2) and 4-dimethylaminopyridine (3) as catalyst in the presence of dipolarophiles
Generation of Nitrile Oxides via O-Tributylstannyl Aldoximes; Application to the Synthesis of Isoxazolines and Isoxazoles
Moriya, Osamu,Takenaka, Hideo,Iyoda, Masaichi,Urata, Yoshikiyo,Endo, Takeshi
, p. 413 - 418 (2007/10/02)
Nitrile oxides were generated readily by the reaction of aldoximes 1, with tert-butyl hypochlorite and bis(tributyltin) oxide.The reaction proceeded efficiently under mild conditions, in which O-stannylated aldoximes 2 are thought to be key intermediates.This reaction system was applicable to the one-pot syntheses of isoxazole derivatives 4 and 5 in the presence of dipolarophiles via a cycloaddition.
O-Ethoxycarbonyl Hydroximoyl Chloride as Nitrile Oxide Precursor
Shimizu, Tomio,Hayashi, Yoshiyuki,Furukawa, Nobuhiro,Teramura, Kazuhiro
, p. 318 - 320 (2007/10/02)
O-Ethoxycarbonyl hydroximoyl chloride serves as a stable precursor for nitrile oxide and is converted into the 1,3-dipole when heated under reflux in pyridine.
