203731-16-2Relevant academic research and scientific papers
Oxidation of N-benzyl-N-methylhydroxylamines to nitrones. A mechanistic study
Hassan, Azfar,Wazeer, Mohammed I. M.,Ali, Sk. Asrof
, p. 393 - 399 (2007/10/03)
Oxidation of various N-(o-, m-, p- substituted benzyl)- N-methylhydroxylamines has been carried out using mercury(II) oxide and p-benzoquinone (p-BQ) as oxidants. Hammett plots have been obtained with negative ρ values, showing the development of a positive centre in the transition state. The unstable E nitrones, which readily isomerize to the more stable Z nitrones, are obtained in appreciable quantities and in some cases as the major product. A considerable deuterium isotope effect is observed in the oxidation process. The overall picture of the mechanistic pathway involves electron transfer from nitrogen to the oxidant followed by hydrogen abstraction.
