Synthesis of Nitrosobenzene Derivatives via Nitrosodesilylation Reaction

The Journal of Organic Chemistry
Corinna KohlmeyerGerhard Hilt

Abstract

The electrophilic ipso-substitution of trimethylsilyl-substituted benzene derivatives into nitrosobenzene derivatives is reported. The optimization of the reaction conditions was performed for moderately electron-deficient, electron-rich, and sterically hindered starting materials by varying reaction time, temperature, and equivalents of NOBF4. Also, a stable intermediate of the nitrosation reaction could be characterized by 19F NMR which can be assigned to a NO+ adduct with the nitrosobenzene derivative. This complex decomposes upon aqueous workup and liberates the desired nitrosobenzene derivative.

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Citations

Apr 7, 2020·Journal of the American Chemical Society·Amit DahiyaFranziska Schoenebeck

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