Methoxylamine oxidation

Oxidation of methoxylamine and some other O-substituted hydroxylamines by lead tetraacetate in the presence of alkenes can also lead to the formation of aziridines. The oxidation of 2,4-dinitrobenzenesul-fenamide is analogous.In view of the results reported widi aminolactams, these reactions do not necessarily establish the intomediacy of nitrenes in the oxidations. 

Hydroxylamine acts as a reducing agent when absorbed systemically, producing methemoglobin and the formulation of Heinz bodies in the blood. It can induce hemolytic anemia. It inhibits platelet aggregation and is a nitric oxide vasodilator. Oxy-Imines such as hydroxylamine and methoxylamine disturb DNA replication and act as potent mutagens, causing nucleotide transition from one purine to another or one pyrimidine to another. 

Fig. 7 Metabolism of compound 13 to reactive hemiacetal metabolites via oxidation of the tetrahydrofuran ring and identification of these reactive species via trapping with methoxylamine...

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