The Journal of organic chemistry

Nitromethane with IBX/TBAF as a nitrosating agent: synthesis of nitrosamines from secondary or tertiary amines under mild conditions

HK Potturi, RK Gurung, Y Hou

Index: Potturi, Hima K.; Gurung, Ras K.; Hou, Yuqing Journal of Organic Chemistry, 2012 , vol. 77, # 1 p. 626 - 631

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Citation Number: 8

Abstract

Aliphatic or aromatic N, N-disubstituted nitrosamine was generated in fair to excellent yield from the reaction of a secondary or tertiary amine with o-iodoxybenzoic acid (IBX) or o- iodosylbenzoic acid (IBA)/R4NX (X= halide) and nitromethane. The product yield was strongly influenced by both the halide of R4NX and iodanes. IBX gave a higher yield than IBA, while the halides follow F–> Cl–> Br–∼ I–. Nitrous acid formed in situ from ...