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| “黑洞型”缺电子联吡啶环蕃的合成 | |
| 引用本文： | 席海涛,孙小强,魏海林,孟启,潘毅,胡宏纹.“黑洞型”缺电子联吡啶环蕃的合成[J].有机化学,2007,27(12):1547-1551. |
| 作者姓名： | 席海涛 孙小强 魏海林 孟启 潘毅 胡宏纹 |
| 作者单位： | 1. 南京大学化学化工学院,南京,210093;江苏工业学院精细石油化工重点实验室,常州,213164 2. 江苏工业学院精细石油化工重点实验室,常州,213164 3. 南京大学化学化工学院,南京,210093 |
| 基金项目： | 国家自然科学基金(No.20272019)，江苏省高校研究生创新计划(2006)资助项目 |
| 摘 要： | 利用2,3,5,6-四氟-1,4-苯二甲酸为原料, 经过酯化、还原及溴代, 合成1,4-二溴甲基-2,3,5,6-四氟苯. 以其为原料在低温下利用模板效应合成高度缺电子的“黑洞型”缺电子联吡啶环蕃化合物, 经过连续液液萃取及离子交换得到“黑洞型”缺电子联吡啶环蕃单体. 产品经1H NMR, 13C NMR, MS表征. 利用变温核磁共振技术研究“黑洞型”缺电子联吡啶环蕃与经典的双环(百草枯-对苯撑)型缺电子联吡啶环蕃在溶液中的变化. |
| 关 键 词： | 2 3 5 6-四氟-1 4-苯二甲酸 1 4-二溴甲基-2 3 5 6-四氟苯 模板效应 黑洞型 环蕃 变温核磁共振 |
| 收稿时间： | 2007-03-14 |
| 修稿时间： | 2007-09-18 |
Synthesis of "Black Hole" 4,4'-Bipyridinium Cyclophane |
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| XI,Hai-Tao,SUN,Xiao-Qiang,WEI,Hai-Lin,MENG,Qi,PAN,Yi,HU,Hong-Wen.Synthesis of "Black Hole" 4,4''''-Bipyridinium Cyclophane[J].Chinese Journal of Organic Chemistry,2007,27(12):1547-1551. | |
| Authors: | XI Hai-Tao SUN Xiao-Qiang WEI Hai-Lin MENG Qi PAN Yi HU Hong-Wen |
| Affiliation: | ( Department of Chemistry, Nanjing University, Nanjing 210093)( Key Laboratory of Fine Chemical Engineering, Jiangsu Polytechnic University, Changzhou 213164) |
| Abstract: | The 4,4'-bipyridinium-based cyclophane cyclo(paraquat-2,3,5,6-tetrafluoro-p-phenylene-paraquat) was prepared by the template-directed synthesis in a 21% yield, of which the starting material 1,4-bis(bromomethyl)-2,3,5,6-tetrafluorobenzene was prepared by the esterification of 2,3,5,6-tetrafluoro-p-phthalic acid with methanol, reduction with LiAlH4 to give 1,4-bis(hydroxymethyl)-2,3,5,6-tetrafluoro-benzene, and then bromination with toluene and 48% HBr. The free cyclophane was characterized by MS, 1H NMR and 13C NMR spectra. The influence of fluorine on the cyclophane in solution was studied by dy-namic 1H NMR spectroscopy. |
| Keywords: | 2 3 5 6-tetrafluoro-p-phthalic acid 1 4-bis(bromomethyl)-2 3 5 6-tetrafluorobenzene template black hole cyclophane dynamic 1H NMR spectroscopy |
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