Highly Ordered Rectangular Columnar Ionic Liquid Crystals: A More Efficient Medium for Intramolecular Diels Alder Reactions

被引：10

作者：

Do, Dat Tien ^{[1
]}

Schmitzer, Andreea R. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, 2900 Edouard Montpetit,CP 6128 Succ Ctr Ville, Montreal, PQ H3C 3J7, Canada

来源：

CHEMISTRYSELECT | 2016年 / 1卷 / 10期

关键词：

ionic liquid crystals; imidazolium salts; intramolecular Diels Alder reaction; recyclability; CLICK REACTIONS; POLYMERS; SALTS; ANION; ACID;

D O I：

10.1002/slct.201600713

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we present the synthesis, the thermal and mesophormic properties of trialkyl(1,3,5-benzene)trisimidazolium salts. These salts form highly ordered rectangular columnar ionic liquid crystal phases and can be used as reaction media for Diels Alder reactions. The use of the ionic liquid crystal phase favours the formation of the intramolecular Diels Alder products, even in high concentration reaction conditions. We show that the ionic liquid crystal phase can be recycled and reused as solvent for at least 10 times, without any loss of yield or selectivity in the Diels Alder reaction.

引用

页码：2448 / 2453

页数：6

共 31 条

[1] Thermotropic Ionic Liquid Crystals [J].

Axenov, Kirill V. ;

Laschat, Sabine .

MATERIALS, 2011, 4 (01) :206-259

[2] A rationalization of the solvent effect on the Diels-Alder reaction in ionic liquids using multiparameter linear solvation energy relationships [J].

Bini, Riccardo ;

Chiappe, Cinzia ;

Mestre, Veronica Llopsis ;

Pomelli, Christian Silvio ;

Welton, Thomas .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (14) :2522-2529

[3] Ionic liquid crystals [J].

Binnemans, K .

CHEMICAL REVIEWS, 2005, 105 (11) :4148-4204

[4] Predicting the hygroscopicity of imidazolium-based ILs varying in anion by hydrogen-bonding basicity and acidity [J].

Cao, Yuanyuan ;

Chen, Yu ;

Wang, Xiaojing ;

Mu, Tiancheng .

RSC ADVANCES, 2014, 4 (10) :5169-5176

[5] The solvent effect on the Diels-Alder reaction in ionic liquids: multiparameter linear solvation energy relationships and theoretical analysis [J].

Chiappe, Cinzia ;

Malvaldi, Marco ;

Pomelli, Christian Silvio .

GREEN CHEMISTRY, 2010, 12 (08) :1330-1339

[6]

Chowdari NS, 2003, SYNLETT, P1906

[7] STEREOSPECIFIC TOTAL SYNTHESIS OF GIBBERELLIC-ACID - KEY TRICYCLIC INTERMEDIATE [J].

COREY, EJ ;

DANHEISER, RL ;

CHANDRASEKARAN, S ;

SIRET, P ;

KECK, GE ;

GRAS, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (25) :8031-8034

[8] Synthesis of tadpole polymers via triple click reactions: Copper-catalyzed azide-alkyne cycloaddition, diels-alder, and nitroxide radical coupling reactions [J].

Dedeoglu, Tuba ;

Durmaz, Hakan ;

Hizal, Gurkan ;

Tunca, Umit .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2012, 50 (10) :1917-1925

[9] Intramolecular Diels Alder reactions in highly organized imidazolium salt-based ionic liquid crystals [J].

Do, Tien Dat ;

Schmitzer, Andreea R. .

RSC ADVANCES, 2015, 5 (01) :635-639

[10] The importance of Green Chemistry in Process Research and Development [J].

Dunn, Peter J. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) :1452-1461

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