55556-85-9Relevant academic research and scientific papers
THE OXIDATION OF HYDROXYLAMINE BY FREMY'S SALT. PREPARATION OF N-NITROSAMINES AND TETRAZENES
Tato, M. P. Vazquez,Castedo, Luis,Riguera, Ricardo
, p. 623 - 626 (2007/10/02)
Treatment of secondary amines with Fremy's salt in aqueous sodium carbonate solution and in the presence of hydroxylamine gives a high yield of either N-nitrosamines or sym-tetrazenes.A mechanism for these conversions is proposed.
Oxidation of N-Nitrosodibenzylamine and Related Compounds by Metalloporphyrin-catalysed Model Systems for the Cytochrome P450 Dependent Mono-oxygenases
Smith, John R. Lindsay,Nee, Michael W.,Noar, J. Barry,Bruice, Thomas C.
, p. 255 - 260 (2007/10/02)
N-Nitrosodibenzylamine has been oxidised to benzaldehyde and benzyl alcohol by iodosylbenzene, 3-chloroperoxybenzoic acid and t-butyl hydroperoxide catalysed by tetraphenylporphyrinato-iron(III) chloride or -manganese(III) chloride.The influence of reaction conditions on the product yields and distribution have been studied.Kinetic isotope effects have been measured with deuteriated N-nitrosodibenzylamines for inter- and intra-molecular competition for the oxidants.The evidence presented is in favour of the iodosylbenzene and t-butyl hydroperoxide oxidations being initiated by hydrogen-atom abstraction by the oxidant from the α-hydrogen of the benzyl group.However, oxidations by the peroxy acid systems may proceed by an initial electron transfer.The reactions of N-nitrosodimethylamine and N-nitrosopiperidine with the metalloporphyrin-catalysed systems show that these substrates are surprisingly unreactive towards oxidation.
