1116-54-7Relevant articles and documents
Facile Formation of N-Nitrosamines from Bromonitromethane and Secondary Amines
Challis, Brian C.,Yousaf, Taher I.
, p. 1598 - 1599 (1990)
Bromonitromethane readily converts secondary amines to N-nitrosamines in aqueous and organic solvents at room temperature via reaction of an iminium ion intermediate with nitrite ion.
Carcinogenic nitrosamines: Hundred-gram preparations of N-nitrosodiethylamine and α-ureidodimethylnitrosamine
Johnston,McCaleb
, p. 311 - 313 (1984)
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Versatile new reagent for nitrosation under mild conditions
Galloway, Jordan D.,Sarabia, Cristian,Fettinger, James C.,Hratchian, Hrant P.,Baxter, Ryan D.
supporting information, p. 3253 - 3258 (2021/05/06)
Here 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 with 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 confirm that 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 effects.
Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation
Kim, Hun Young,Oh, Kyungsoo,Si, Tengda
, p. 9216 - 9221 (2019/10/08)
ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.