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Radical decomposition of N,N-bis-(3-chloro-1,4-naphthoquinon-2-yl) amine in basic conditions followed by EPR

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EPR spectroscopy was used to assess the radicals produced upon basic decomposition of N,N-bis-(3-chloro-1,4-naphthoquinon-2-yl) amine (BClNQA). Three radicals have been trapped and identified: N′-bis(3-chloro-1,4-naphthoquinone) hydrazine radical (6), 2-hydroxy-3-chloro-1,4-naphthoquinone anion radical (9) and 2-amino-3-chloro-1,4-naphthoquinone radical (8). The probable reaction mechanism, the structure of intermediates as well as the reaction profile are discussed.


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