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Reduction of Nitroarenes to Azoxybenzenes by Potassium Borohydride in Water
School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China
School of Science, Beijing Jiaotong University, Beijing 100044, China
Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, IL 62026, USA
* Author to whom correspondence should be addressed.
Received: 24 February 2011; in revised form: 15 April 2011 / Accepted: 22 April 2011 / Published: 28 April 2011
Abstract: The synthesis of the azoxybenzenes by the reduction of nitroarenes with reducing agent potassium borohydride in water was reported for the first time. PEG-400 was used as a phase transfer catalyst and could effectively catalyze the reduction. The electronic effects of substituent groups play an important role in determining the reduction efficiencies. Electron-withdrawing substituents promote the formation of the azoxybenzene products, while electron-releasing groups retard the reductions to various degrees depending on the extent of their electron-donating ability.
Keywords: nitroarenes; azoxybenzenes; potassium borohydride; water; PEG-400
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Cite This Article
MDPI and ACS Style
Liu, Y.; Liu, B.; Guo, A.; Dong, Z.; Jin, S.; Lu, Y. Reduction of Nitroarenes to Azoxybenzenes by Potassium Borohydride in Water. Molecules 2011, 16, 3563-3568.
Liu Y, Liu B, Guo A, Dong Z, Jin S, Lu Y. Reduction of Nitroarenes to Azoxybenzenes by Potassium Borohydride in Water. Molecules. 2011; 16(5):3563-3568.
Liu, Yufang; Liu, Bo; Guo, Ailing; Dong, Zhenming; Jin, Shuo; Lu, Yun. 2011. "Reduction of Nitroarenes to Azoxybenzenes by Potassium Borohydride in Water." Molecules 16, no. 5: 3563-3568.