Sonochemical cycloadditions in ionic liquids.: Lessons from model cases involving common dienes and carbonyl dienophiles

被引：29

作者：

Bravo, Jose Luis ^{[1
]}

Lopez, Ignacio

Cintas, Pedro

Silvero, Guadalupe

Arevalo, Maria Jose

机构：

[1] Univ Extremadura, Dept Quim Organ, E-10071 Caceres, Spain

[2] Univ Extremadura, Dept Quim Organ, E-06071 Badajoz, Spain

来源：

ULTRASONICS SONOCHEMISTRY | 2006年 / 13卷 / 05期

关键词：

Diels-Alder; green chemistry; ionic liquids; organic synthesis; sonochemical cycloaddition;

D O I：

10.1016/j.ultsonch.2005.07.001

中图分类号：

O42 [声学];

学科分类号：

070206 [声学]; 082403 [水声工程];

摘要：

This contribution describes a series of sonochemical cycloadditions involving either cyclopentadiene or 1,3-cyclohexadiene with carbonyl dienophiles in an imidazolium-based ionic liquid as reaction medium. In general, ultrasound does effectively improve these processes in terms of higher yields and/or shorter reaction times when compared with the corresponding silent reactions. Stereoselectivities, however, remain practically unaffected by sonication. The role of ionic liquids under ultrasonic activation is also discussed. (c) 2605 Published by Elsevier B.V.

引用

页码：408 / 414

页数：7

共 40 条

[1]

Formation and stability of N-heterocyclic carbenes in water:: The carbon acid pKa of imidazollum cations in aqueous solution [J].

Amyes, TL ;

Diver, ST ;

Richard, JP ;

Rivas, FM ;

Toth, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4366-4374

[2]

[Anonymous], DIELSALDER REACTION

[3]

Thermal and sonochemical studies on the Diels-Alder cycloadditions of masked o-benzoquinones with furans:: New insights into the reaction mechanism [J].

Avalos, M ;

Babiano, R ;

Cabello, N ;

Cintas, P ;

Hursthouse, MB ;

Jiménez, JL ;

Light, ME ;

Palacios, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) :7193-7203

[4]

Ultrasound promoted C-C bond formation: Heck reaction at ambient conditions in room temperature ionic liquids [J].

Deshmukh, RR ;

Rajagopal, R ;

Srinivasan, KV .

CHEMICAL COMMUNICATIONS, 2001, (17) :1544-1545

[5]

ULTRASOUND IN ORGANIC-SYNTHESIS .13. SOME FUNDAMENTAL-ASPECTS OF THE SONOCHEMICAL BARBIER REACTION [J].

DESOUZABARBOZA, JC ;

PETRIER, C ;

LUCHE, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1212-1218

[6]

On the noninnocent nature of 1,3-dialkylimidazolium ionic liquids [J].

Dupont, J ;

Spencer, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (40) :5296-5297

[7]

Fillion H, 1998, SYNTHETIC ORGANIC SONOCHEMISTRY, P91

[8]

Thermophysical properties of imidazolium-based ionic liquids [J].

Fredlake, CP ;

Crosthwaite, JM ;

Hert, DG ;

Aki, SNVK ;

Brennecke, JF .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2004, 49 (04) :954-964

[9]

POTENTIOMETRIC INVESTIGATION OF DIALUMINUM HEPTACHLORIDE FORMATION IN ALUMINUM CHLORIDE 1-BUTYLPYRIDINIUM CHLORIDE MIXTURES [J].

GALE, RJ ;

OSTERYOUNG, RA .

INORGANIC CHEMISTRY, 1979, 18 (06) :1603-1605

[10]

Biodegradable ionic liquids: Part I. Concept, preliminary targets and evaluation [J].

Gathergood, N ;

Garcia, MT ;

Scammells, PJ .

GREEN CHEMISTRY, 2004, 6 (03) :166-175

← 1 2 3 4 →