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Reaction of Halogenonitrobenzenes with Electro-generated Superoxide Ion

Authors :
Tetsuo Osa
Hiromitsu Sagae
Katsutaro Komazawa
Masamichi Fujihira
Henning Lund
Source :
Bulletin of the Chemical Society of Japan. 53:2188-2194
Publication Year :
1980
Publisher :
The Chemical Society of Japan, 1980.

Abstract

The reaction of halogenonitrobenzenes (XNBs) with electrogenerated superoxide ion in N,N-dimethylformamide was studied electrochemically using cyclic voltammetry (CV) and controlled potential macro-electrolysis. It was shown in the CV that electro-generated superoxide ion reacts with all of the o- and p-isomers of iodo-, bromo-, and chloronitrobenzene in the dissolved oxygen medium. However the superoxide ion did not react with the other XNBs during CV. Controlled potential macro-electrolysis of oxygen in the presence of o- and p-bromonitrobenzene yielded the corresponding nitrophenols as the main products. The reaction mechanism via nucleophilic attack of the superoxide ion on the XNB, in the preference to an electron-transfer mechanism, is proposed.

Details

ISSN :
13480634 and 00092673
Volume :
53
Database :
OpenAIRE
Journal :
Bulletin of the Chemical Society of Japan
Accession number :
edsair.doi...........09e3b8f8b2a41240c35446eec448da17
Full Text :
https://doi.org/10.1246/bcsj.53.2188