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Synthesis of Nitrosamines

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A practical and efficient N-nitrosation of secondary amines was achieved using the [NO+·Crown·H(NO3)2-] complex, with easy preparation, handling, and complete solubility in dichloromethane. This relatively stable and efficient reagent acts as a source of nitrosonium ions (NO+) under mild and homogeneous conditions. 18-Crown-6 can be recycled and reused.
M. A. Zolfigol, M. H. Zebarjadian, G. Chehardoli, H. Keypour, S. Salehzadeh, M. Shamsipur, J. Org. Chem., 2001, 66, 3619-3620.


In a mild, iodide-catalyzed process to synthesize N-nitrosamines from amines and nitromethane using TBHP as the oxidant, the catalytic system succeeded in cleaving the carbon-nitrogen bond in nitromethane. This methodology uses commercially available, inexpensive catalysts and oxidants and has a wide substrate scope and operational simplicity.
J. Zhang, J. Jiang, Y. Li, X. Wan, J. Org. Chem., 2013, 78, 11366-11372.


A N-nitrososulfonamide can be used as chemical reagent for transnitrosation under mild experimental conditions. This reagent is stable to air and moisture across a broad range of temperatures and offers high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. The sulfonamide byproduct is easily recovered to regenerate the reagent.
J. D. Galloway, C. Sarabia, J. C. Fettinger, H. P. Hratchian, R. D. Baxter, Org. Lett., 2021, 23, 3253-3258.


tert-Butyl nitrite (TBN) is a multitask reagent for the controlled synthesis of N-nitrosoamides from N-alkyl amides, hydrolysis of N-methoxyamides to carboxylic acids, metal-free benzocoumarin synthesis from ortho-aryl-N-methoxyamides, and Ru-catalyzed isocoumarin synthesis.
S. L. Yedage, B. M. Bhanage, J. Org. Chem., 2017, 82, 5769-5781.