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Iodide-Catalyzed Synthesis of N-Nitrosamines via C-N Cleavage of Nitromethane

Jie Zhang, Jiewen Jiang, Yuling Li and Xiaobing Wan*

*Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People’s Republic of China, Email:

J. Zhang, J. Jiang, Y. Li, X. Wan, J. Org. Chem., 2013, 78, 11366-11372.

DOI: 10.1021/jo401915t (free Supporting Information)

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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.

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Key Words

Nitrosamines, TBHP

ID: J42-Y2013