33499-41-1Relevant academic research and scientific papers
One-pot synthesis of oxime ethers from benzaldehyde or acetophenone, hydroxylamine salt, potassium hydroxide, and alkyl halides
Li, Chunbao,Zhang, Hang,Cui, Yi,Zhang, Shuanming,Zhao, Zheyuan,Choi, Michael C. K.,Chan, Albert S. C.
, p. 543 - 546 (2007/10/03)
Oxime ethers were synthesized in one-pot reaction from benzaldehyde or acetophenone, hydroxylamine hydrogen chloride, alkyl halides and KOH in aqueous DMSO. The reactions were completed in 15-50 min with yields in 80-96%.
Photolytic and radical induced decompositions of O-alkyl aldoxime ethers
McCarroll, Andrew J.,Walton, John C.
, p. 1868 - 1875 (2007/10/03)
Direct photolytic radical induced homolyses of O-alkyl arylaldoxime ethers (ArCH=NOR) were studied by EPR spectroscopy and by end product analyses. Initiating radicals (X·), including t-BuO·, t-BuS· , alkyl and Me3Sn·, added rapidly to the C=N double bond to give adduct oxyaminyl radicals (ArCHXN·OR) that could be observed and characterised by EPR spectroscopy. For O-alkyl arylaldoxime ethers containing H-atoms attached to the carbon adjacent to the ether oxygen (OR = OCHR12), t-BuO· radicals also abstracted this hydrogen to yield oxyalky radicals that underwent rapid β-scission to afford iminyl radicals (ArCHN·) and an aldehyde or ketone (R12CO). judged by the relative importance of ROH and ArCN amongst the products, abstraction of the iminyl hydrogen atom also took place to yield oximidoyl radicals (ArC·=NOR), although this could not be confirmed by EPR spectroscopic observation of these radicals. Thus, homolysis induced by t-BuO· radicals took place comparatively unselectively. Addition of the t-BuO· radical to the C=N double bond of oxime ethers was very fast, the rate constant being comparable to that for addition of the same radical to nitrones. Direct and photosensitised UV photolysis of O-alkyl arylaldoxime ethers gave alkoxyl and aryliminyl radicals in very low yields. Although traces of 2-methyl-tetrahydrofuran were detected from cyclisation of the pent-4-enyloxyl radical generated by direct photolysis of O-pent-4-enyl benzaldoxime, yields were too low for preparative purposes.
