17019-28-2Relevant articles and documents
A convenient synthesis of 3-benzoylisoxazoles by 1,3-dipolar cycloaddition
Kai, Hiroyuki,Tomida, Minoru,Nakai, Toru,Takase, Akira
, p. 2299 - 2308 (2007/10/03)
A convenient, efficient method for the preparation of 3-benzoylisoxazoles is described. Nitrile oxides generated in situ from phenylglyoxylohydroxamyl chlorides and NaHCO3 in isopropyl alcohol smoothly react with dipolarophiles at room temperat
Preparation and mechanism of solvolysis of N-hydroxy-α- oxobenzeneethanimidoyl chloride, a 2-(hydroxyimino)-1-phenylethan-1-one derivative: Molecular structure of α-oxo-oximes (=α-(hydroxyimino) ketones)
Hamersak, Zdenko,Peric, Berislav,Kojic-Prodic, Biserka,Cotarca, Livius,Delogu, Pietro,Sunjic, Vitomir
, p. 1289 - 1301 (2007/10/03)
Acid-catalyzed methanolysis of N-hydroxy-α-oxobenzeneethanimidoyl chloride (1), a 2-(hydroxyimino)-1-phenylethan-1-one derivative obtained in one step from acetophenone, leads to a constant ratio of methyl α- oxobenzeneacetate (2) and methyl α-(hydroxyimino)benzeneacetate (3). 13C(α) Labelled [13C]-1 affords 13C(α) labelled [13C]-3, thus discarding the hypothesis of its formation via 1,2-arene migration. The reported sequence opens a novel approach to phenylglyoxylic and mandelic acid esters (=α-oxobenzeneacetic and α-hydroxybenzeneacetic acid esters), from acetophenone. The molecular structures of 1 and 3 were determined by X-ray structure analysis and compared with previously reported crystallographic data of α-oxo-oximes (=α-(hydroxyimino) ketones) 4 and 6-8. The unique stereoelectronic characteristics of the α-oxo-oxime moiety are discussed. All α-oxo-oximes share the following structural characteristics: (E)- configuration of the oxime C=N-OH bond (i.e. OH and C=O trans), the s-trans conformation of the oxo and imino moieties about the C(α)-C(=NOH) single bond, and intermolecular H-bonding. They differ from the isostructural α- diketone enols by the absence of resonance-assisted intramolecular H-bonding.
NEW SYNTHESES OF α-OXIMINO-α-HALOKETONES : REACTIONS OF α-HALOKETONES WITH ALKYL THIONITRITES
Kim, Yong Hae,Jung, Sun Ho
, p. 2371 - 2372 (2007/10/02)
α-Oximo-α-haloketones were readily synthesized in good yields by treating α-haloketone with alkyl thionitrites under mild conditions.