Base-mediated rearrangement of free aromatic hydroxamic acids (ArCO–NHOH) to anilines

Y Hoshino, M Okuno, E Kawamura, K Honda…

Index: Hoshino, Yujiro; Okuno, Moriaki; Kawamura, Eri; Honda, Kiyoshi; Inoue, Seiichi Chemical Communications, 2009 , # 17 p. 2281 - 2283

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Citation Number: 13

Abstract

We were therefore quite surprised to observe in the course of our investigation to explore an alternative synthetic method for N-arylhydroxamic acids via copper-catalyzed N-arylation with aryl iodide 10 that free benzohydroxamic acid, without addition of external activating agent, could be converted to aniline in moderate yield, which means occurrence of C to N migration of the aryl group (eqn (1)). This amazing result prompted us to investigate the literature on the ...

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