The role of hydrogen bonding in controlling the selectivity of Diels-Alder reactions in room-temperature ionic liquids

被引：292

作者：

Aggarwal, A ^{[1
]}

Lancaster, NL ^{[1
]}

Sethi, AR ^{[1
]}

Welton, T ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci & Technol, Dept Chem, London SW7 2AY, England

来源：

GREEN CHEMISTRY | 2002年 / 4卷 / 05期

关键词：

D O I：

10.1039/b206472c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of cyclopentadiene with methyl acrylate has been investigated in a range of ionic liquids. The origin of the endo-selectivity for the reactions and associated rate enhancements has been attributed to a hydrogen bond formed between the cation of the ionic liquid and the methyl acrylate.

引用

页码：517 / 520

页数：4

共 29 条

[1] Quaternary ammonium zinc- or tin-containing ionic liquids: water insensitive, recyclable catalysts for Diels-Alder reactions
Abbott, AP
Capper, G
Davies, DL
Rasheed, RH
Tambyrajah, V
[J]. GREEN CHEMISTRY, 2002, 4 (01) : 24 - 26
[2] Upon the Hydrogen-Bonding Ability of the H4 and H5 Protons of the Imidazolium Cation
Abdul-Sada, Ala'a K.
Al-Juaid, Salih
Greenway, Anthony M.
Hitchcock, Peter B.
Howells, Matthew J.
Seddon, Kenneth R.
Welton, Thomas
[J]. STRUCTURAL CHEMISTRY, 1990, 1 (04) : 391 - 394
[3] EVIDENCE FOR HYDROGEN-BONDING IN SOLUTIONS OF 1-ETHYL-3-METHYLIMIDAZOLIUM HALIDES, AND ITS IMPLICATIONS FOR ROOM-TEMPERATURE HALOGENOALUMINATE(III) IONIC LIQUIDS
AVENT, AG
CHALONER, PA
DAY, MP
SEDDON, KR
WELTON, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1994, (23): : 3405 - 3413
[4] CORRELATION OF SOLVENT EFFECTS ON STEREOSELECTIVITIES OF DIELS-ALDER REACTIONS BY MEANS OF LINEAR FREE ENERGY RELATIONSHIPS - A NEW EMPIRICAL MEASURE OF SOLVENT POLARITY
BERSON, JA
MUELLER, WA
HAMLET, Z
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (02) : 297 - &
[5] HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER
BRESLOW, R
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) : 159 - 164
[6] Cammarata L, 2001, PHYS CHEM CHEM PHYS, V3, P5192, DOI 10.1039/b106900d
[7] SOLVENT EFFECTS ON ENDO/EXO-SELECTIVITIES AND REGIO-SELECTIVITIES OF DIELS-ALDER REACTIONS OF CARBONYL-CONTAINING DIENOPHILES
CATIVIELA, C
GARCIA, JI
MAYORAL, JA
SALVATELLA, L
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (04): : 847 - 851
[8] CROWHURST L, UNPUB ANAL CHEM
[9] Expanding the polarity range of ionic liquids
Dzyuba, SV
Bartsch, RA
[J]. TETRAHEDRON LETTERS, 2002, 43 (26) : 4657 - 4659
[10] Diels-Alder reactions in ionic liquids - A safe recyclable alternative to lithium perchlorate-diethyl ether mixtures
Earle, MJ
McCormac, PB
Seddon, KR
[J]. GREEN CHEMISTRY, 1999, 1 (01) : 23 - 25

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