70416-62-5Relevant academic research and scientific papers
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.
Regio- and stereochemistry of [2 + 2] photocycloadditions of imines to alkenes: A computational and experimental study
Sampedro, Diego,Soldevilla, Alberto,Campos, Pedro J.,Ruiz, Roberto,Rodriguez, Miguel A.
scheme or table, p. 8331 - 8336 (2009/04/11)
(Chemical Equation Presented) The [2 + 2] photocycloaddition of isoxazolines to alkenes has been studied by means of CASPT2/6-31G*// CASSCF/6-31G*. The reaction outcome is influenced by the relative ratio of imine deactivation and photocycloaddition. Anal
Isolation of nitrile oxides from the thermal fragmentation of furazan N-oxides
Mitchell, William R.,Paton, R.Michael
, p. 2443 - 2446 (2007/10/07)
Flash vacuum pyrolysis of furoxans generates nitrile oxides, which have been reacted with alkenes to yield 2-isoxazolines, and have been examined by 1H and 13C nmr spectroscopy.
