High-performance Liquid Chromatography Study of the Nitration Course of Tetrabutoxycalix[4]arene at the Upper Rim:Determination of the Optimum Conditions for the Preparation of 5,11,17-Trinitro-25,26,27,28-tetrabutoxycalix[4]arene |
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| Authors: | LI Zhengyi MA Jiejie CHEN Jiawen PAN Yi JIANG Juli WANG Leyong |
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| Institution: | 1. Key Laboratory of Mesoscopic Chemistry of Ministry of Education,School of Chemistry and Chemical Engineering,Nanjing University,Nanjing,Jiangsu 210093,China
2. State Key Laboratory of Coordination Chemistry,Nanjing University,Nanjing,Jiangsu 210093,China |
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| Abstract: | A selective nitration of calix4]arene at the upper rim in one pot process was described by monitoring the time dependence of the distribution of products by high‐performance liquid chromatography (HPLC). The discrimination of five nitrated products was accomplished by molecular symmetry considerations and 1H NMR analysis. As a result, unusual 5,11,17‐trinitrocalix4]arene ( 2d ) was obtained in 57% isolated yield. 5,11‐Dinitro‐calix4]arene ( 2b ) and 5,11,17‐trinitrocalix4]arene ( 2d ) with tetranitrocalix4]arene 2e were further characterized by crystal X‐ray diffraction analysis. Furthermore, as an example of potential application, trinitrocalix4]arene 2d could be converted to triaminocalix4]arene 3d conveniently. |
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| Keywords: | calix[4]arene selective nitration high-performance liquid chromatography |
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