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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
Author(s) -
Hansen John F.,
Georgiou Paul J.
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310634
Subject(s) - chemistry , nitrosation , oxime , nitro , medicinal chemistry , peroxynitrite , oxide , organic chemistry , alkyl , enzyme , superoxide
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‐4 H ‐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.