作者:E. Boyland、R. Nery
DOI:10.1039/j39660000354
日期:——
The oxidation of alkyl or benzyl N-hydroxycarbamate produced mainly the corresponding O-alkoxycarbonyl or O-benzoxycarbonyl N-hydroxycarbamates and small amounts of the corresponding trisubstituted hydroxylamines. The oxidation of sodium benzhydroxamate with iodine gave O-benzoyl benzhydroxamate; hydroxyurea and N-hydroxy-N′-phenylurea were similarly converted into N-carbamoyloxyurea and N-hydroxy-N′-phenyl-N-phenylcarbamoylurea, respectively. Oxidation of ethyl, n-propyl, and benzyl N-hydroxycarbamates or hydroxyurea of N-hydroxy-N-phenylurea with iodine in aqueous ammonium carbonate gave the corresponding carbamates, urea, or phenylurea. With silver oxide in ether, alkyl N-hydroxycarbamates and their O-alkoxycarbonyl derivatives yielded N-silver-N-alkoxycarbonyloxycarbamates; simulataneous oxidation of ethyl and benzyl N-hydroxycarbamates gave NO-di- and NNO-tri-substituted hydroxylamines in which the substituents were ethoxycarbonyl, benzyloxycarbonyl, or, possibly, ethyl and benzyl groups.
烷基或苄基N-羟基氨基甲酸酯的氧化主要生成相应的O-烷氧羰基或O-苄氧羰基N-羟基氨基甲酸酯,以及少量相应的三取代羟基胺。碘氧化苯甲基羟肟酸钠生成O-苯甲酰基苯甲基羟肟酸;羟基脲和N-羟基-N'-苯基脲同样分别转化为N-氨基甲酸羟基脲和N-羟基-N'-苯基-N-苯基氨基甲酸羟基脲。在水合碳酸铵中用碘氧化乙基、正丙基和苄基N-羟基氨基甲酸酯或羟基脲以及N-羟基-N-苯基脲,生成相应的氨基甲酸酯、脲或苯脲。在乙醚中用氧化银氧化,烷基N-羟基氨基甲酸酯及其O-烷氧羰基衍生物生成N-银-N-烷氧羰基羟基氨基甲酸酯;同时氧化乙基和苄基N-羟基氨基甲酸酯,生成NO-二取代和NNO-三取代的羟基胺,其中取代基为乙氧羰基、苄氧羰基,或可能是乙基和苄基。