Regioselective alkylation of a methylene group via meta-bridging of calix[4]arenes

被引:8
作者
Slavik, Petr [1 ]
Dvorakova, Hana [2 ]
Eigner, Vaclav [3 ]
Lhotak, Pavel [1 ]
机构
[1] Prague Inst Chem Technol, Dept Organ Chem, CR-16628 Prague 6, Czech Republic
[2] ICTP, Lab NMR Spect, Prague, Czech Republic
[3] ICTP, Dept Solid State Chem, Prague, Czech Republic
关键词
SUBSTITUTION; CALIXARENES;
D O I
10.1039/c4cc04356a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The meta-iodo derivative, fixed in the cone conformation, enables the gram-scale preparation of a meta-bridged calix[4]arene. This intermediate, possessing a fluorene moiety within the macrocyclic skeleton, can be regioselectively alkylated on the corresponding methylene bridge to form a unique substitution pattern in classical calixarene chemistry.
引用
收藏
页码:10112 / 10114
页数:3
相关论文
共 17 条
[1]   Synthesis of bifluorenes via cobalt halide radical coupling [J].
Al-Afyouni, Malik H. ;
Huang, Tiffany A. ;
Hung-Low, Fernando ;
Bradley, Christopher A. .
TETRAHEDRON LETTERS, 2011, 52 (26) :3261-3265
[2]   CALIXARENES, MACROCYCLES WITH (ALMOST) UNLIMITED POSSIBILITIES [J].
BOHMER, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :713-745
[3]   Synthesis and reactions of a 2-chlorocalix[4]arene and a 2,2′-coupled dicalixarene [J].
Carroll, Louise T. ;
Hill, P. Aru ;
Ngo, Chinh Q. ;
Klatt, Kenneth P. ;
Fantini, Jordan L. .
TETRAHEDRON, 2013, 69 (24) :5002-5007
[4]   Easily accessible symmetrically and unsymmetrically bridge disubstituted tetrahydroxycalix[4]arenes in advantageous trans-cone conformation [J].
Fischer, Conrad ;
Katzsch, Felix ;
Weber, Edwin .
TETRAHEDRON LETTERS, 2013, 54 (22) :2874-2877
[5]   Structural conditions required for the bridge lithiation and substitution of a basic calix[4]arene [J].
Fischer, Conrad ;
Seichter, Wilhelm ;
Weber, Edwin .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :1602-1608
[6]   Bridge-disubstituted calix[4]arenes obtained via a new preparative route. Synthesis and structural study [J].
Fischer, Conrad ;
Lin, Guisheng ;
Seichter, Wilhelm ;
Weber, Edwin .
TETRAHEDRON, 2011, 67 (31) :5656-5662
[7]   meta-Bridged calix[4] arenes: a straightforward synthesis via organomercurial chemistry [J].
Flidrova, Karolina ;
Slavik, Petr ;
Eigner, Vaclav ;
Dvorakova, Hana ;
Lhotak, Pavel .
CHEMICAL COMMUNICATIONS, 2013, 49 (60) :6749-6751
[8]   CALIX[4]ARENES WITH ALKYLIDENE BRIDGES, SYNTHESIS AND CONFORMATIONAL PROPERTIES [J].
GRUTTNER, C ;
BOHMER, V ;
VOGT, W ;
THONDORF, I ;
BIALI, SE ;
GRYNSZPAN, F .
TETRAHEDRON LETTERS, 1994, 35 (34) :6267-6270
[9]  
Gutsche CD, 2008, MONOGR SUPRAMOL CHEM, P1, DOI 10.1039/9781847558190-FP001
[10]   Synthesis and 'click' cycloaddition reactions of tetramethoxy- and tetrapropoxy-2-(ω-azidoalkyl)calix[4]arenes [J].
Hardman, Michael J. ;
Thomas, Ashley M. ;
Carroll, Louise T. ;
Williams, Linus C. ;
Parkin, Sean ;
Fantini, Jordan L. .
TETRAHEDRON, 2011, 67 (37) :7027-7034