91154-16-4Relevant academic research and scientific papers
Generation of nitrile oxides from oximes using t -BuOI and their cycloaddition
Minakata, Satoshi,Okumura, Sota,Nagamachi, Toshiki,Takeda, Youhei
supporting information; experimental part, p. 2966 - 2969 (2011/07/07)
tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cycloaddition of oximes and alkenes/alkynes, leading to the formation of a variety of isoxazolines or isoxazoles under mild conditions.
Flash vacuum pyrolysis of 1,2,5-oxadiazole 2-oxides and 1,2,3-triazole 1-oxides
Mitchell, William R.,Paton, R. Michael
experimental part, p. 34 - 54 (2011/02/21)
The flash vacuum pyrolysis (FVP, 450-600 °C/10-3 mmHg) of 3,4-diaryl- and 3,4-dialkyl-1,2,5-oxadiazole 2-oxides (furoxans) has been investigated. In all cases the 1,2,5-oxadiazole ring cleaved cleanly at O(1)-N(2) and C(3)-C(4) to afford two nitrile oxide fragments, which were trapped in high yield (75-97%) as their isoxazoline cycloadducts by reaction with alk-1-enes. At higher temperatures (700-800 °C) isocyanates were formed as by-products. The dimerisation of acetonitrile oxide to dimethylfuroxan was followed by 1H NMR spectroscopy, and the rate constant for the 2 nd order reaction determined. The furoxans were converted into isocyanates in good yield (61-95%) by FVP, followed by sulfur dioxide-mediated isomerisation of the resulting nitrile oxides. 2,4,5-Trisubstituted-1,2,3- triazole 1-oxides showed greater thermal stability, but at 700-800 °C decomposition of the 4,5-dimethyl compound 25b lead to 1,2-di(5-methyl-2-phenyl- 1,2,3-triazol-2-yl)ethane as the major product; attempts to trap acetonitrile oxide were unsuccessful. ARKAT USA, Inc.
SYNTHESIS OF ISOXAZOLINES AND ISOXAZOLES FROM ALDOXIMES BY THE USE OF SODIUM BROMITE WITH ORGANOTIN HALIDE
Moriya, Osamu,Nakamura, Hideki,Kageyama, Toshifumi,Urata, Yoshikiya
, p. 3987 - 3990 (2007/10/02)
The oxidizing system using sodium bromite with a catalytic amount of tri-n-butyltin chloride is applied for the preparations of isoxazolines and isoxazoles from aldoximes via dipolar cycloaddition.
