17952-96-4Relevant articles and documents
Preparation of 4-Bromo-1-hydroxypyrazole 2-Oxides by Nitrosation of α-Bromo-α,β-unsaturated Ketoximes
Hansen, John F.,Easter, John A.,Eckert, David A.,Hunt, Karen J.,Little, David A.
, p. 281 - 286 (2007/10/02)
Nitrosation of the oximes of 3-bromo-3-penten-2-one, 3-bromo-4-phenyl-3-buten-2-one, and 2-bromo-1,3-diphenyl-2-propen-1-one using sodium nitrite in acetic acid gave low yields of 4-pyrazolone 1,2-dioxides.Nitrosation using butyl nitrite in the presence of copper(II) sulfate and pyridine in aqueous ethanol produced insoluble copper complexes from which 3,5-dimethyl-, 3-methyl-5-phenyl-, and 3,5-diphenyl-4-bromo-1-hydroxypyrazole 2-oxides could be liberated by treatment with dilute potassium hydroxide, filtration, and acidification of the filtrate.High yields wereobtained with the first two oximes, but, presumably due to unfavorable stereochemistry of the oxime, the diphenyl derivative gave a lower yield of the complex, accompanied by 4-bromo- and 4-nitro-3,5-diphenylisoxazole and 4-oximino-3,5-diphenyl-4,5-dihydroisoxazole.
Nitrosation of Methyl and Phenyl Styryl Ketoximes Under Oxygen. Formation of 4-Nitro-1-hydroxypyrazole 2-Oxides and 3,5-Diphenyl-4-nitrato-4,5-dihydroisoxazole
Hansen, John F.,Georgiou, Paul J.
, p. 1487 - 1492 (2007/10/02)
The nitrosation of the oximes of 4-phenyl-3-buten-2-one and 1,3-diphenyl-2-propen-1-one under oxygen has been reinvestigated.In addition to 4-oxo- and 4-oximino-4H-pyrazole 1,2-dioxides previously reported, the reactions give 4-nitro-1-hydroxypyrazole 2-oxides.In the case of 1,3-diphenyl-2-propen-1-one oxime the nitrosation reaction also gives 3,5-diphenyl-4-nitrato-4,5-dihydroisoxazole.Evidence is presented suggesting that the nitrate ester is formed through the rearrangement of a peroxynitrite intermediate.