Diels-Alder reactions in chloroaluminate ionic liquids: Acceleration and selectivity enhancement

被引：208

作者：

Lee, CW ^{[1
]}

机构：

[1] Tennessee State Univ, Dept Chem, Nashville, TN 37209 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(99)00249-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The utility of room temperature chloroaluminate ionic liquids as solvent and catalyst for the synthetically important Diels-Alder reaction was studied. The AlCl3-1-ethyl-3-methyl-1H-imidazolium chloride medium proved to be ideally suited for Diels-Alder reactions. Endo selectivity and rate enhancement were observed for the cyclopentadiene/methyl acrylate Diels-Alder reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2461 / 2464

页数：4

共 11 条

[1] ON THE ORIGIN OF PRODUCT SELECTIVITY IN AQUEOUS DIELS-ALDER REACTIONS [J].

BRESLOW, R ;

MAITRA, U .

TETRAHEDRON LETTERS, 1984, 25 (12) :1239-1240

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

BRESLOW, R ;

MAITRA, U ;

RIDEOUT, D .

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

[3]

HOOK KN, 1973, J AM CHEM SOC, V95, P4094

[4] ROOM-TEMPERATURE HALOALUMINATE IONIC LIQUIDS - NOVEL SOLVENTS FOR TRANSITION-METAL SOLUTION CHEMISTRY [J].

HUSSEY, CL .

PURE AND APPLIED CHEMISTRY, 1988, 60 (12) :1763-1772

[5] DIELS-ALDER REACTIONS IN ETHYLAMMONIUM NITRATE, A LOW-MELTING FUSED SALT [J].

JAEGER, DA ;

TUCKER, CE .

TETRAHEDRON LETTERS, 1989, 30 (14) :1785-1788

[6]

Kiselev VD., 1989, RUSS CHEM REV, V58, P230, DOI DOI 10.1070/RC1989V058N03ABEH003437

[7] ACCELERATION AND SELECTIVITY ENHANCEMENT OF DIELS-ALDER REACTIONS BY SPECIAL AND CATALYTIC METHODS [J].

PINDUR, U ;

LUTZ, G ;

OTTO, C .

CHEMICAL REVIEWS, 1993, 93 (02) :741-761

[8] HYDROPHOBIC ACCELERATION OF DIELS-ALDER REACTIONS [J].

RIDEOUT, DC ;

BRESLOW, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (26) :7816-7817

[9] SOLVENT EFFECTS ON THE MECHANISM AND SELECTIVITIES OF ASYMMETRIC DIELS-ALDER REACTIONS [J].

RUIZLOPEZ, MF ;

ASSFELD, X ;

GARCIA, JI ;

MAYORAL, JA ;

SALVATELLA, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (19) :8780-8787

[10] QUANTITATIVE STUDY OF THE ACIDITY OF HCL IN A MOLTEN CHLOROALUMINATE SYSTEM (ALCL3 1-ETHYL-3-METHYL-1H-IMIDAZOLIUM CHLORIDE) AS A FUNCTION OF HCL PRESSURE AND MELT COMPOSITION (51.0-66.4 MOL-PERCENT ALCL3) [J].

SMITH, GP ;

DWORKIN, AS ;

PAGNI, RM ;

ZINGG, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5075-5077

← 1 2 →