ACCELERATION IN WATER OF THE BAYLIS-HILLMAN REACTION

被引：84

作者：

AUGE, J ^{[1
]}

LUBIN, N ^{[1
]}

LUBINEAU, A ^{[1
]}

机构：

[1] UNIV PARIS 11,CNRS,CHIM ORGAN MULTIFONCT LAB,F-91405 ORSAY,FRANCE

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 43期

关键词：

D O I：

10.1016/0040-4039(94)80018-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DABCO-catalyzed coupling reaction of benzaldehyde with acrylonitrile was greatly accelerated in water compared to usual organic solvents. The reaction was even more accelerated by adding lithium or sodium iodide in the aqueous medium. Other structured solvents also enhanced the reaction, but to a smaller extent.

引用

页码：7947 / 7948

页数：2

共 13 条

[1] RATE ENHANCEMENT EFFECTS IN THE DABCO CATALYZED SYNTHESIS OF HYDROXYALKENOATE ESTERS [J].

AMEER, F ;

DREWES, SE ;

FREESE, S ;

KAYE, PT .

SYNTHETIC COMMUNICATIONS, 1988, 18 (05) :495-500

[2] A KINETIC AND MECHANISTIC STUDY OF THE BAYLIS-HILLMAN REACTION [J].

BODE, ML ;

KAYE, PT .

TETRAHEDRON LETTERS, 1991, 32 (40) :5611-5614

[3] HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164

[4] IMPROVED SYNTHESES OF ETHYL ALPHA-(BROMOMETHYL)ACRYLATE AND 2-METHYLENE-1,3-PROPANEDIOL VIA ETHYL ALPHA-(HYDROXYMETHYL)ACRYLATE [J].

BYUN, HS ;

REDDY, KC ;

BITTMAN, R .

TETRAHEDRON LETTERS, 1994, 35 (09) :1371-1374

[5] SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES [J].

DREWES, SE ;

ROOS, GHP .

TETRAHEDRON, 1988, 44 (15) :4653-4670

[6] A PRIORI COMPUTATION OF A SOLVENT-ENHANCED SN2 REACTION PROFILE IN WATER - THE MENSHUTKIN REACTION [J].

GAO, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7796-7797

[7] FUNCTIONALIZATION OF THE ALPHA-POSITION OF ACRYLATE SYSTEMS BY THE ADDITION OF CARBONYL-COMPOUNDS - HIGHLY PRESSURE-DEPENDENT REACTIONS [J].

HILL, JS ;

ISAACS, NS .

TETRAHEDRON LETTERS, 1986, 27 (41) :5007-5010

[8]

HILL JS, 1988, J CHEM RES S, P330

[9] HIGHLY DIASTEREOSELECTIVE COUPLING REACTIONS BETWEEN CHIRAL BENZALDEHYDE TRICARBONYLCHROMIUM COMPLEXES AND ACTIVATED DOUBLE-BONDS [J].

KUNDIG, EP ;

XU, LH ;

ROMANENS, P ;

BERNARDINELLI, G .

TETRAHEDRON LETTERS, 1993, 34 (44) :7049-7052

[10]

KUNDU MK, 1994, SYNLETT, P444

← 1 2 →