Citation: LIU Yan-Zhu*, HUANG Yi-Ning, LI Xia, ZHANG Ling, LI Yong-Xiu*. Coordination-Mediated Radical Nitration of Methyl Salicylate by Copper(Ⅱ) Nitrate with High Regioselectivity[J]. Chinese Journal of Inorganic Chemistry, ;2014, 30(1): 121-126. doi: 10.11862/CJIC.2014.037 shu

Coordination-Mediated Radical Nitration of Methyl Salicylate by Copper(Ⅱ) Nitrate with High Regioselectivity

1.
Department of Chemistry, School of Science, Nanchang University, Jiangxi 330031, China

Received Date: 26 September 2013
Available Online: 4 November 2013
Fund Project:

High yield and para-selective products were obtained by the nitration of methyl salicylate (MeS) and copper(Ⅱ) nitrate(CuN). The results of electron absorption spectra (EAS),Cyclic Voltammetry(CV) and electrospray ionization mass spectra (ESIMS) reveal that the reaction favors a radical nitration mechanism. It is the coordination of MeS with CuNthat promotes the splitting of N-O bonds of nitrate group in CuN, and results in the formation of nitro radicals, oxygen radicals and complex radicals. The nitro radicals can react with MeS or the complexes of MeS to form nitration products. The nitrated complexes immediately turn to methyl nitrosalicylate by Cu(Ⅱ) ions being hydrolyzed to copper(Ⅱ) oxides.
- methyl salicylate;Cu(Ⅱ) nitrate;radical nitration;coordination,
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沈阳化工大学材料科学与工程学院沈阳 110142