57527-63-6Relevant academic research and scientific papers
Oxidation of N,N'-Dialkyl-1,2-bishydroxylamines
Weiss, Randy H.,Furfine, Eric,Hausleden, Edward,Dixon, Dabney White
, p. 4969 - 4972 (2007/10/02)
Oxidation of N,N'-dialkyl-1,2-bishydroxylamines RNHOCH2CH2ONHR gives products that are a function of oxidant.For R = i-Pr (5) and m-chloroperbenzoic acid the products are diisopropyl azo dioxide, HOCH2CH2ONHCH(CH3)2, and ethylene glycol.Product ratios indicate independent oxidation of the two hydroxylamine functions.Na2WO4/H2O2 in D2O gives the azo dioxide, ethylene glycol, and acetone oxime.Oxidation with bromine and 1,4-diazabicyclooctane or tert-butyl hypochlorite and triethylamine gives product ratios that are consistent with two pathways to the bis oxime 7: one that appears to give 7 directly and a second that goes through the monohydroxylamine monooxime 15.It is proposed that the former reaction proceeds through the 1,4,2,3-dioxadiazine ring, which is oxidized quickly to products.Reaction products from the bishydroxylamine with R = CH3 are similar to those with R = i-Pr.
