Meyers Institute for Interdisciplinary Research in Organic and Medicinal Chemistry and Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, Illinois 62901, United States.
J Org Chem. 2012 Jan 6;77(1):626-31. doi: 10.1021/jo202276x. Epub 2011 Dec 19.
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)/R(4)NX (X = halide) and nitromethane. The product yield was strongly influenced by both the halide of R(4)NX and iodanes. IBX gave a higher yield than IBA, while the halides follow F(-) > Cl(-) > Br(-) ∼ I(-). Nitrous acid formed in situ from nitromethane and IBX (or IBA)/halides is likely responsible for the observed reaction.
脂肪族或芳香族 N,N-二取代亚硝胺可以由仲胺或叔胺与邻碘酰基苯甲酸（IBX）或邻碘代过氧苯甲酸（IBA）/R(4)NX（X = 卤素）和硝基甲烷反应生成，产率适中到很高。产物的产率受到 R(4)NX 和碘烷的卤素的强烈影响。IBX 的产率高于 IBA，而卤素则遵循 F(-) > Cl(-) > Br(-) ∼ I(-)。由硝基甲烷和 IBX（或 IBA）/卤化物原位形成的亚硝酸可能是导致观察到的反应的原因。
