Issue 6, 2004
From the journal:

Chemical Communications

Reduction of nitroaromatics to arylnitrenium ions by vinyl halide cations†

Hao Chen,a   Xubin Zheng,a   Pengxiang Yanga  and  R. Graham Cooks*a  

* Corresponding authors

a Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA
E-mail: cooks@purdue.edu
Fax: (765) 494-9421
Tel: (765) 494-5263

Abstract

The title reduction of nitroaromatics ArNO2 by vinyl halide radical cations CH2[double bond, length as m-dash]CH–X+˙ (X = Cl or Br) to form arylnitrenium ions ArNH+ involves a change in oxidation number of nitrogen from +3 to −1. This novel reaction provides a new route for the generation of arylnitrenium ions, a highly selective method for the detection of explosives in mixtures, and offers clues to the carcinogenic activity of nitroaromatics in vivo.

Graphical abstract: Reduction of nitroaromatics to arylnitrenium ions by vinyl halide cations

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Article information

DOI
https://doi.org/10.1039/B314713D
Article type
Communication
Submitted
14 Nov 2003
Accepted
24 Dec 2003
First published
12 Feb 2004

Chem. Commun., 2004, 688-689

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Reduction of nitroaromatics to arylnitrenium ions by vinyl halide cations

H. Chen, X. Zheng, P. Yang and R. G. Cooks, Chem. Commun., 2004, 688 DOI: 10.1039/B314713D

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