Organic Chemistry

A Versatile New Reagent for Nitrosation under Mild Conditions



We report a new chemical reagent for transnitrosation under mild experimental conditions. This new reagent is stable to air and moisture across a broad range of temperatures, and is effective for transnitrosation in multiple solvents. Compared to traditional nitrosation methods, our reagent shows high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. Several challenging nitroso-compounds are accessed here for the first time, including 15N isotopologues. X-ray data confirms two rotational isomers of the reagent are configurationally stable at room temperature, although only one isomer is effective for transnitrosation. Computational analysis describes the energetics of rotamer interconversion, including interesting geometry-dependent hybridization ef-fects.


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Supplementary material

Thumbnail image of Computational SI4.pdf
Computational SI4
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Baxter Nitrosation Reagent