Nonacidic nitration of secondary amines

JC Bottaro, RJ Schmitt, CD Bedford

Index: Bottaro, Jeffrey C.; Schmitt, Robert J.; Bedford, Clifford D. Journal of Organic Chemistry, 1987 , vol. 52, # 11 p. 2292 - 2294

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Citation Number: 13

Abstract

The N-nitration of secondary amines under neutral conditions poses a unique problem of N- nitrosation as a competing side reaction. When nitrogen dioxide, l nitryl chloride,* nitrogen pentoxide, nitryl fluoride, nitronium flu~ roborate,~ and tetranitromethane* are used in the N- nitration of amines, they all result in substantial yields (230%) of nitrosamine side products, which are extremely toxic and difficult to separate from the target nitramines. Nitramines ...