What is the proposed mechanism for the formation of 2-aminophenoxazine-3-one from 2-aminophenol?

Label:chem

Topic
A study discusses the detailed mechanism of the oxidation of 2-aminophenol to 2-aminophenoxazine-3-one using (diacetoxyiodo)benzene.
Answer
The formation of 2-aminophenoxazine-3-one involves a radical reaction pathway. Two competitive pathways are proposed: one involving the formation of an oxygen-bridged intermediate and the other involving a nitrogen-bridged intermediate. The oxygen-bridged pathway is favored, and the process is accelerated by the presence of a third radical species, such as a methoxy radical, which can facilitate hydrogen atom transfer.
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