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Synthesis of Nitrosamines

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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.


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.