3378-36-7Relevant articles and documents
On the Oxidation of Hydroxylamines with o -Iodoxybenzoic Acid (IBX)
Parmeggiani, Camilla,Matassini, Camilla,Cardona, Francesca,Goti, Andrea
, p. 2890 - 2900 (2017/06/27)
o -Iodoxybenzoic acid (IBX) is confirmed as a powerful tool for the oxidation of hydroxylamines. The synthetic route is demonstrated as efficient and user friendly, and is exploited on various carbohydrate-derived N,N-disubstituted hydroxylamines (cyclic, acyclic, and functionalized ones), affording the corresponding nitrones in good yields and regioselectivity. N-Monosubstituted hydroxylamines revealed an interesting divergent behavior depending on the reaction conditions. While IBX oxidation in dimethyl sulfoxide at 45 °C furnished oximes as reported, the oxidation in dichloromethane at room temperature afforded efficiently the unusual corresponding nitroso dimers.
Synthesis and X-ray Analysis of Dihydro-1,2,4,5-trioxazine. Evidence of a Steowise Mechanism for the Cycloaddition of Carbonyl Oxides with Nitrones
Mori, Mitsuyuki,Sugiyama, Tomohito,Nojima, Masatomo,Kusabayashi, Shigekazu,McCullough, Kevin J.
, p. 2285 - 2294 (2007/10/02)
Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo cycloaddition reactions with nitrones affording dihydro-1,2,4,5-trioxazines in fair to excellent yield.The structures of dihydro-3,5,6-triphenyl-1,2,4,5-trioxazine (5f) and dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine (5t) were unambiguously determined by X-ray analysis.Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)- or (Z)-α-(4-methylphenyl)-α-phenyl-N-methylnitrone gave a 1:1 mixture of two stereoisomeric cycloadducts.This result, in conjunction with the structure of the relevant 5t, suggests that the cycloaddition proceeds by a stepwise mechanism.
