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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
Author(s) -
Li Zhengyi,
Ma Jiejie,
Chen Jiawen,
Pan Yi,
Qiang Juli,
Wang Leyong
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990341
Subject(s) - nitration , chemistry , yield (engineering) , high performance liquid chromatography , chromatography , organic chemistry , materials science , metallurgy
A selective nitration of calix[4]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 1 H NMR analysis. As a result, unusual 5,11,17‐trinitrocalix[4]arene ( 2d ) was obtained in 57% isolated yield. 5,11‐Dinitro‐calix[4]arene ( 2b ) and 5,11,17‐trinitrocalix[4]arene ( 2d ) with tetranitrocalix[4]arene 2e were further characterized by crystal X‐ray diffraction analysis. Furthermore, as an example of potential application, trinitrocalix[4]arene 2d could be converted to triaminocalix[4]arene 3d conveniently.