Synthesis of 3,5‐Diarylated 4‐Cyano‐2‐nitrophenols via Nitro Rearrangement

ABSTRACT

3,5‐Diaryl‐4‐cyano‐4‐nitrocyclohexanones underwent bromination upon treatment with bromine and ammonium acetate. When the resulting dibromocyclohexanones were stirred in pyridine, dehydrobromination followed by nitro rearrangement occurred to furnish unsymmetrically functionalized 3,5‐diarylated 4‐cyano‐2‐nitrophenols. Computational studies suggested that the rearrangement proceeds either through a concerted pathway or via a radical‐pair intermediate.