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Switchable Selectivity during Oxidation of Anilines in a Ball Mill
Author(s) -
Thorwirth Rico,
Bernhardt Franziska,
Stolle Achim,
Ondruschka Bernd,
Asghari Jila
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001702
Subject(s) - azoxy , ball mill , selectivity , grinding , solvent , chemistry , nitro , microwave , organic chemistry , materials science , combinatorial chemistry , metallurgy , catalysis , computer science , telecommunications , alkyl
A solvent‐free method for the direct oxidation of anilines to the corresponding azo and azoxy homocoupling products by using a planetary ball mill was developed. Various oxidants and grinding auxiliaries were tested and a variety of substituted anilines were investigated. It was possible to form chemoselectively either azo, azoxy, or the nitro compounds from reaction of aromatic anilines. The selectivity of the solvent‐free reaction is switchable by applying a combination of oxidant and grinding auxiliary. Furthermore, a comparison with other methods of energy input (microwave, classical heating, and ultrasound) highlighted the advantages of the ball mill approach and its high energy efficiency.