2017/06/07 by Camilla Matassini, Andrea Goti, Camilla Parmeggiani +1 · 1 citation
Chemistry · #Catalysis #Chemical Synthesis and Reactions #Chemistry #Combinatorial chemistry #Dichloromethane #Organic chemistry #Oxidative Organic Chemistry Reactions #Regioselectivity #Solvent #Sulfoxide #Vanadium and Halogenation Chemistry
paper · doi:10.1055/s-0036-1588457
openalex publication_date 2017/06/07 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/04
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.