18315-79-2Relevant articles and documents
Highly stereoselective nitration of chalcone derivatives with nitric oxide
Li, Rui,Liu, Zhongquan,Zhou, Yulu,Wu, Longmin
, p. 1367 - 1368 (2006)
A novel nitration of chalcone derivatives with nitric oxide affords E-α-nitropropenones exclusively in good yield. The reaction is most likely initiated by electrophilic addition of nitric dioxide to the C=C double bond at the α-position. Georg Thieme Ver
Synthetic Diversity from a Versatile and Radical Nitrating Reagent
Zhang, Kun,Jelier, Benson,Passera, Alessandro,Jeschke, Gunnar,Katayev, Dmitry
supporting information, p. 12929 - 12939 (2019/09/17)
We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C?H diversification of alkenes and alkynes. Beyond furnishing a library of aryl β-nitroalkenes, this reagent provides unparalleled access to β-nitrohydrins and β-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N?N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, electron paramagnetic resonance spectroscopy, we observed direct evidence of a nitryl radical in solution by nitrone spin-trapping. To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C?H partners to prepare isoxazolines and isoxazoles is presented. This approach allows for the formation of an in situ nitrile oxide from a ketone partner, the presence of which is detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeds in a single-operational step using a mild, regioselective, and general protocol with broad chemoselectivity.
Research in antitumor chemotherapy. XII. Correlation between ethylenimine addition and cytotoxic action on tumor cells of compounds with activated ethylenic double bonds
Dore,Viel
, p. 666 - 672 (2007/10/05)
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