title: Nitromethane with IBX/TBAF as a nitrosating agent: synthesis of nitrosamines from secondary or tertiary amines under mild conditions.
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)/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.
authors.affiliation: Meyers Institute for Interdisciplinary Research in Organic and Medicinal Chemistry and Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, Illinois 62901, United States.
authors.forename: Hima K
authors.initials: HK
authors.lastname: Potturi
authors.forename: Ras K
authors.initials: RK
authors.lastname: Gurung
authors.forename: Yuqing
authors.initials: Y
authors.lastname: Hou
mesh_terms: D000588:Amines / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009595:Nitroparaffins / Q000737:chemistry*; D009602:Nitrosamines / Q000138:chemical synthesis*; D015538:Nitrosation
chemical_list: D000588:Amines; D007462:Iodobenzenes; D009595:Nitroparaffins; D009602:Nitrosamines; C476101:o-iodoxybenzoic acid; D008697:Methane; C008640:nitromethane