Abstract

Abstract In alkaline solution, 4-nitrophenyl N-hydroxycarbamate undergoes reaction by elimination to yield 4-nitrophenoxide ion, and by rearrangement to yield N-carboxy-4-nitrophenoxyamine. The effect of pH on the yield of the rearrangement product establishes that a transient spiro Meisenheimer complex is formed reversibly. Aromatization of this species occurs by two competing pH-independent reactions: one involves expulsion of a hydroxamate ion; the other involves the formation of a carbamate ion via a general base catalyzed collapse of the complex.

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