Nitromethane with IBX/TBAF as a Nitrosating Agent: Synthesis of Nitrosamines from Secondary or Tertiary Amines under Mild Conditions

被引：27

作者：

Potturi, Hima K.

Gurung, Ras K.

Hou, Yuqing ^{[1
]}

机构：

[1] So Illinois Univ, Meyers Inst Interdisciplinary Res Organ & Med Che, Carbondale, IL 62901 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 01期

关键词：

N; N-DIALKYL AROMATIC-AMINES; NORMAL-BUTYL NITRITE; N-NITROSATION; HETEROGENEOUS CONDITIONS; EFFICIENT METHOD; DEALKYLATION; REAGENT; IODINE; ACID; NITRATION;

D O I：

10.1021/jo202276x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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- similar to I-. Nitrous acid formed in situ from nitromethane and IBX (or IBA)/halides is likely responsible for the observed reaction.

引用

页码：626 / 631

页数：6

共 43 条

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