Synthesis of pillar[7]arene

被引:42
作者
Chen, Yu [1 ]
Tao, Hong Qi [1 ]
Kou, Yu Hui [1 ]
Meier, Herbert [2 ]
Fu, Jian Long [1 ]
Cao, De Rong [1 ]
机构
[1] S China Univ Technol, Sch Chem & Chem Engn, State Key Lab Luminescent Mat & Devices, Guangzhou 510641, Peoples R China
[2] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55099 Mainz, Germany
基金
中国国家自然科学基金;
关键词
Pillar[n]arenes; Pillar[7]arene; Host-guest chemistry; Condensation reaction; Iron(III) chloride; COMPLEXATION;
D O I
10.1016/j.cclet.2012.03.026
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first synthesis of pillar[7]arene is reported with two methods. Method A: the FeCl3-catalyzed condensation reaction of 1,4-dimethoxybenzene (1) with paraformaldehyde in CHCl3 gave dimethoxypillar[7]arene (3). Method B: the p-toluenesulfonic acid catalyzed condensation reaction of 2,5-bis(benzyloxymethyl)-1,4-dimethoxybenzene (2) in CH2Cl2 gave compound 3. Demethylation of 3 with BBr3 gave pillar[7]arene (4). The pillar[7]arene might be a perspective macrocyclic host in host-guest chemistry. (C) 2012 De Rong Cao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码:509 / 511
页数:3
相关论文
共 11 条
[1]   A Facile and Efficient Preparation of Pillararenes and a Pillarquinone [J].
Cao, Derong ;
Kou, Yuhui ;
Liang, Jianquan ;
Chen, Zhizhao ;
Wang, Lingyun ;
Meier, Herbert .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9721-9723
[2]  
Chen Z.X., 2011, TETRAHEDRON LETT, V52, P2484
[3]   Pillar[5]arenes: fascinating cyclophanes with a bright future [J].
Cragg, Peter J. ;
Sharma, Kushal .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (02) :597-607
[4]   DIBPillar[n]arenes (n=5, 6): Syntheses, X-ray Crystal Structures, and Complexation with n-Octyltriethyl Ammonium Hexafluorophosphate [J].
Han, Chengyou ;
Ma, Fengying ;
Zhang, Zibin ;
Xia, Binyuan ;
Yu, Yihua ;
Huang, Feihe .
ORGANIC LETTERS, 2010, 12 (19) :4360-4363
[5]  
Huang F.H., 2011, ANGEW CHEM INT EDIT, V50, P1397
[6]   Complexation of 1,4-Bis(pyridinium)butanes by Negatively Charged Carboxylatopillar[5]arene [J].
Li, Chunju ;
Shu, Xiaoyan ;
Li, Jian ;
Chen, Songhui ;
Han, Kang ;
Xu, Min ;
Hu, Bingjie ;
Yu, Yihua ;
Jia, Xueshun .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (20) :8458-8465
[7]   Efficient synthesis of copillar[5]arenes and their host-guest properties with dibromoalkanes [J].
Liu, Luzhi ;
Cao, Derong ;
Jin, Yi ;
Tao, Hongqi ;
Kou, Yuhui ;
Meier, Herbert .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (20) :7007-7010
[8]   para-bridged symmetrical pillar[5]arenes:: Their Lewis acid catalyzed synthesis and host-guest property [J].
Ogoshi, Tomoki ;
Kanai, Suguru ;
Fujinami, Shuhei ;
Yamagishi, Tada-aki ;
Nakamoto, Yoshiaki .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (15) :5022-5023
[9]   Monofunctionalized Pillar[5]arene as a Host for Alkanediamines [J].
Strutt, Nathan L. ;
Forgan, Ross S. ;
Spruell, Jason M. ;
Botros, Youssry Y. ;
Stoddart, J. Fraser .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5668-5671
[10]   Synthesis and host-guest properties of pillar[6]arenes [J].
Tao HongQi ;
Cao DeRong ;
Liu Luzhi ;
Kou YuHui ;
Wang LingYun ;
Meier, Herbert .
SCIENCE CHINA-CHEMISTRY, 2012, 55 (02) :223-228