Spectacular Rate Enhancement of the Diels-Alder Reaction at the Ionic Liquid/n-Hexane Interface

被引：15

作者：

Beniwal, Vijay ^{[1
]}

Manna, Arpan ^{[1
]}

Kumar, Anil ^{[1
]}

机构：

[1] CSIR Natl Chem Lab, Phys & Mat Chem Div, Pune 411008, Maharashtra, India

来源：

CHEMPHYSCHEM | 2016年 / 17卷 / 13期

关键词：

Diels-Alder reaction; interfaces; ionic liquids; kinetics; stereoselectivity; ORGANIC-SYNTHESIS; ON-WATER; HUISGEN CYCLOADDITIONS; IN-WATER; TEMPERATURE; RATIONALIZATION; ACCELERATION; SUSPENSIONS; CATALYSIS; SALT;

D O I：

10.1002/cphc.201600006

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The use of the ionic liquid/n-hexane interface as a new class of reaction medium for the Diels-Alder reaction gives large rate enhancements of the order of 10(6) to 10(8) times and high stereoselectivity, as compared to homogeneous media. The rate enhancement is attributed to the H-bonding abilities and polarities of the ionic liquids, whereas the hydrophobicity of ionic liquids was considered to be the factor in controlling stereoselectivity.

引用

页码：1969 / 1972

页数：4

共 34 条

[1] Quaternary ammonium zinc- or tin-containing ionic liquids: water insensitive, recyclable catalysts for Diels-Alder reactions [J].

Abbott, AP ;

Capper, G ;

Davies, DL ;

Rasheed, RH ;

Tambyrajah, V .

GREEN CHEMISTRY, 2002, 4 (01) :24-26

[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] SELECTIVE DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTIONS AND SUSPENSIONS [J].

BRESLOW, R ;

MAITRA, U ;

RIDEOUT, D .

TETRAHEDRON LETTERS, 1983, 24 (18) :1901-1904

[4] Organic synthesis in water: 1,3-dipolar cycloaddition reactions at ambient temperature with aqueous suspensions of solid reactants [J].

Butler, Richard N. ;

Coyne, Anthony G. ;

Moloney, Eamon M. .

TETRAHEDRON LETTERS, 2007, 48 (20) :3501-3503

[5] Understanding "On-Water" Catalysis of Organic Reactions. Effects of H+ and Li+ Ions in the Aqueous Phase and Nonreacting Competitor H-Bond Acceptors in the Organic Phase: On H2O versus on D2O for Huisgen Cycloadditions [J].

Butler, Richard N. ;

Coyne, Anthony G. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) :1809-1817

[6] Water and Organic Synthesis: A Focus on the In-Water and On-Water Border. Reversal of the In-Water Breslow Hydrophobic Enhancement of the Normal endo-Effect on Crossing to On-Water Conditions for Huisgen Cycloadditions with Increasingly Insoluble Organic Liquid and Solid 2π-Dipolarophiles [J].

Butler, Richard N. ;

Coyne, Anthony G. ;

Cunningham, William J. ;

Moloney, Eamon M. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) :3276-3291

[7] Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water" [J].

Butler, Richard N. ;

Coyne, Anthony G. .

CHEMICAL REVIEWS, 2010, 110 (10) :6302-6337

[8] Wetting and Tribological Properties of Ionic Liquids [J].

Castejon, Henry J. ;

Wynn, Troy J. ;

Marcin, Zachary M. .

JOURNAL OF PHYSICAL CHEMISTRY B, 2014, 118 (13) :3661-3668

[9] 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

[10] Diels-Alder reactions in ionic liquids - A safe recyclable alternative to lithium perchlorate-diethyl ether mixtures [J].

Earle, MJ ;

McCormac, PB ;

Seddon, KR .

GREEN CHEMISTRY, 1999, 1 (01) :23-25

← 1 2 3 4 →