Preparation and thermal stability of optically active 1,2,4-triazolium-based ionic liquids

被引：9

作者：

Borowiecki, Pawel ^{[1
]}

Poterala, Marcin ^{[1
]}

Maurin, Jan ^{[2
]}

Wielechowska, Monika ^{[1
]}

Plenkiewicz, Jan ^{[1
]}

机构：

[1] Warsaw Univ Technol, Fac Chem, Noakowskiego St 3, PL-00664 Warsaw, Poland

[2] Natl Ctr Nucl Res, PL-05400 Otwock, Poland

来源：

ARKIVOC | 2012年

关键词：

Optically active ionic liquids; 1,2,4-triazolium salts; kinetic resolution; TRANSFER RADICAL POLYMERIZATION; ASYMMETRIC MICHAEL ADDITION; DESIGN; ORGANOCATALYSTS; RESOLUTION;

D O I：

10.3998/ark.5550190.0013.823

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of optically active ionic liquids, in a four-step reaction sequence, is described. In the first step an oxirane ring of cyclohexene oxide was opened with 1,2,4-triazole, yielding a racemic mixture of (1R,2R)- and (1S,2S)-2-(1H-1,2,4-triazol-1-yl) cyclohexanol. Kinetic resolution of the racemate by a lipase catalyzed transesterification with vinyl acetate followed by alkylation (quaternization) of the triazole ring resulted in the appropriate optically active salts formation. After the anion metathesis, thermally stable novel chiral ionic liquids were obtained.

引用

页码：262 / 281

页数：20

共 47 条

[1] Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis [J].

Baudequin, C ;

Brégeon, D ;

Levillain, J ;

Guillen, F ;

Plaquevent, JC ;

Gaumont, AC .

TETRAHEDRON-ASYMMETRY, 2005, 16 (24) :3921-3945

[2] Design and synthesis of novel ionic liquid/liquid crystals (IL 2Cs) with axial chirality [J].

Baudoux, J ;

Judeinstein, P ;

Cahard, D ;

Plaquevent, JC .

TETRAHEDRON LETTERS, 2005, 46 (07) :1137-1140

[3]

Benson F. R., 1967, TETRAZINES PURINES R, V8, P1

[4] Radical polymerization in a chiral ionic liquid: Atom transfer radical polymerization of acrylates [J].

Biedron, T ;

Kubisa, P .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2005, 43 (15) :3454-3459

[5] Ionic liquids as reaction media for polymerization processes: atom transfer radical polymerization (ATRP) of acrylates in ionic liquids [J].

Biedron, T ;

Kubisa, P .

POLYMER INTERNATIONAL, 2003, 52 (10) :1584-1588

[6]

Borowiecki P., 2010, THESIS

[7] Simple and straightforward synthesis of novel enantiopure ionic liquids via efficient enzymatic resolution of (±)-2-(1H-imidazol-1-yl)cyclohexanol [J].

Busto, Eduardo ;

Gotor-Fernandez, Vicente ;

Rios-Lombardia, Nicolas ;

Garcia-Verdugo, Eduardo ;

Alfonso, Ignacio ;

Garcia-Granda, Santiago ;

Menendez-Velazquez, Amador ;

Burguete, M. Isabel ;

Luis, Santiago V. ;

Gotor, Vicente .

TETRAHEDRON LETTERS, 2007, 48 (30) :5251-5254

[8] Design and synthesis of imidazolinium salts derived from (L)-valine. Investigation of their potential in chiral molecular recognition [J].

Clavier, H ;

Boulanger, L ;

Audic, N ;

Toupet, L ;

Mauduit, M ;

Guillemin, JC .

CHEMICAL COMMUNICATIONS, 2004, (10) :1224-1225

[9] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[10]

Demirayak S, 1998, Pharm Acta Helv, V72, P285, DOI 10.1016/S0031-6865(97)00035-6

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