Diels-Alder reactions in ionic liquids - A safe recyclable alternative to lithium perchlorate-diethyl ether mixtures

被引：549

作者：

Earle, MJ ^{[1
]}

McCormac, PB ^{[1
]}

Seddon, KR ^{[1
]}

机构：

[1] Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland

来源：

GREEN CHEMISTRY | 1999年 / 1卷 / 01期

关键词：

D O I：

10.1039/a808052f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diels-Alder reactions in neutral ionic liquids (such as 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium tetrafluoroborate, and 1-butyl-3-methyl-imidazolium lactate) are reported. Rate enhancements and selectivities similar to those of reactions performed in lithium perchlorate-diethyl ether mixtures have been observed. As the ionic liquids used have no measurable vapour pressure, are thermally robust, will tolerate impurities such as water, and are recyclable, it is envisaged that these systems could be used on an industrial scale.

引用

页码：23 / 25

页数：3

共 19 条

[1] Adams CJ, 1998, CHEM COMMUN, P2097
[2] Reversing the stereochemistry of a Diels-Alder reaction: use of metalloporphyrin oligomers to control transition state stability
Clyde-Watson, Z
Vidal-Ferran, A
Twyman, LJ
Walter, CJ
McCallien, DWJ
Fanni, S
Bampos, N
Wylie, RS
Sanders, JKM
[J]. NEW JOURNAL OF CHEMISTRY, 1998, 22 (05) : 493 - 502
[3] Studies on the use of surfactants in aqueous Diels-Alder reactions
Diego-Castro, MJ
Hailes, HC
[J]. TETRAHEDRON LETTERS, 1998, 39 (15) : 2211 - 2214
[4] THE LITHIUM PERCHLORATE-DIETHYL ETHER RATE ACCELERATION OF THE DIELS-ALDER REACTION - LEWIS ACID CATALYSIS BY LITHIUM ION
FORMAN, MA
DAILEY, WP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) : 2761 - 2762
[5] Ionic liquid crystals: hexafluorophosphate salts
Gordon, CM
Holbrey, JD
Kennedy, AR
Seddon, KR
[J]. JOURNAL OF MATERIALS CHEMISTRY, 1998, 8 (12) : 2627 - 2636
[6] DRAMATIC RATE ACCELERATIONS OF DIELS-ALDER REACTIONS IN 5-M LITHIUM PERCHLORATE DIETHYL-ETHER - THE CANTHARIDIN PROBLEM REEXAMINED
GRIECO, PA
NUNES, JJ
GAUL, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4595 - 4596
[7] DIELS-ALDER REACTION OF METHANESULFONYL CYANIDE WITH CYCLOPENTADIENE - INDUSTRIAL SYNTHESIS OF 2-AZABICYCLO[2.2.1]HEPT-5-ENE-3-ONE
GRIFFITHS, GJ
PREVIDOLI, FE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) : 6129 - 6131
[8] HANDY ST, 1995, SYNLETT, P565
[9] HOLBREY JD, 1998, IN PRESS J CHEM S DA
[10] DIELS-ALDER REACTIONS IN ETHYLAMMONIUM NITRATE, A LOW-MELTING FUSED SALT
JAEGER, DA
TUCKER, CE
[J]. TETRAHEDRON LETTERS, 1989, 30 (14) : 1785 - 1788

← 1 2 →