The paper reports the results of a wide study aimed at preparing aryl chlorides (19 examples), bromides (19 examples), and iodides (9 examples) by halodediazoniation of dry arenediazonium o-benzenedisulfonimides with tetraalkylammonium halides. The reactions were carried out in anhydrous acetonitrile at room temperature (~20 C) in the presence of copper powder and at 60 C or room temperature without the catalyst. In optimal conditions the yields were from good to excellent (60 reactions, 61-94% yield), with only a few exceptions (8 reactions, 51-55% yield). A good amount of the o-benzenedisulfonimide was always recovered from the reactions and could then be reused to prepare arenediazonium salts. An interesting aspect of this research is the surprising role of the anion of o-benzenedisulfonimide as an electron transfer agent.

Halodediazoniations of dry arendiazonium o-benzenedisulfonimides in the presence or absence of an electron transfer catalyst. Easy general procedures to prepare Aryl chlorides,bromides,and iodides

BARBERO, Margherita;DEGANI, Jacopo;DUGHERA, Stefano;FOCHI, Rita
1999-01-01

Abstract

The paper reports the results of a wide study aimed at preparing aryl chlorides (19 examples), bromides (19 examples), and iodides (9 examples) by halodediazoniation of dry arenediazonium o-benzenedisulfonimides with tetraalkylammonium halides. The reactions were carried out in anhydrous acetonitrile at room temperature (~20 C) in the presence of copper powder and at 60 C or room temperature without the catalyst. In optimal conditions the yields were from good to excellent (60 reactions, 61-94% yield), with only a few exceptions (8 reactions, 51-55% yield). A good amount of the o-benzenedisulfonimide was always recovered from the reactions and could then be reused to prepare arenediazonium salts. An interesting aspect of this research is the surprising role of the anion of o-benzenedisulfonimide as an electron transfer agent.
64
3448
3453
dry arendiazonium o-benzenedisulfonimides; halodediazoniation; aryl chlorides; aryl bromides; aryl iodides
BARBERO M.; I. DEGANI; DUGHERA S.; FOCHI R.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/1738
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