Vicarious nucleophilic substitution of hydrogen in nitrophenyl toluenesulfonates

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Abstract

Toluenesulfonates of nitrophenols react with carbanions possessing leaving groups giving products of the vicarious nucleophilic substitution of hydrogen. The yields and orientation depend on the reaction conditions and the structure of the reagents. The products obtained can be easily hydrolyxed to the corresponding phenols or - in certain cases - to hydroxynitrobenzaldehydes.

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Ma̧kosza, M., Ziobrowski, T., Serebriakov, M., & Kwast, A. (1997). Vicarious nucleophilic substitution of hydrogen in nitrophenyl toluenesulfonates. Tetrahedron, 53(13), 4739–4750. https://doi.org/10.1016/S0040-4020(97)00143-9

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