Diels-Alder reactions in water

被引：200

作者：

Otto, S ^{[1
]}

Engberts, JBFN ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

来源：

PURE AND APPLIED CHEMISTRY | 2000年 / 72卷 / 07期

关键词：

D O I：

10.1351/pac200072071365

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This review illustrates how water, as an environmentally friendly solvent, can have significant additional benefits when it is used as a solvent for the Diels-Alder reaction. The mechanism by which the unique properties of water enhance the rate and selectivity are discussed. Also, possibilities for the achievement of further increases in rate and enantioselectivity of aqueous Diels-Alder reactions through Lewis-acid and micellar catalysis are reviewed.

引用

页码：1365 / 1372

页数：8

共 72 条

[1] REGIOCHEMICAL AND STEREOCHEMICAL VARIATIONS IN DIELS-ALDER REACTIONS [J].

ARSENIYADIS, S ;

RODRIGUEZ, R ;

YASHUNSKY, DV ;

CAMARA, J ;

OURISSON, G .

TETRAHEDRON LETTERS, 1994, 35 (27) :4843-4846

[2] ACTIVATION AND REACTION VOLUMES IN SOLUTION [J].

ASANO, T ;

LENOBLE, J .

CHEMICAL REVIEWS, 1978, 78 (04) :407-489

[3]

ASSFELD M, 1995, J CHEM SOC CHEM COMM, P1371

[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 [J].

BERSON, JA ;

MUELLER, WA ;

HAMLET, Z .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (02) :297-&

[5] SOLVENT EFFECTS ON A DIELS-ALDER REACTION FROM COMPUTER-SIMULATIONS [J].

BLAKE, JF ;

JORGENSEN, WL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7430-7432

[6] DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTIONS - ENFORCED HYDROPHOBIC INTERACTIONS BETWEEN DIENE AND DIENOPHILE [J].

BLOKZIJL, W ;

BLANDAMER, MJ ;

ENGBERTS, JBFN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4241-4246

[7]

BLOKZIJL W, 1991, THESIS U GRONINGEN

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

BRESLOW, R ;

MAITRA, U ;

RIDEOUT, D .

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

[9] SOLVENT EFFECTS ON ENDO/EXO-SELECTIVITIES AND REGIO-SELECTIVITIES OF DIELS-ALDER REACTIONS OF CARBONYL-CONTAINING DIENOPHILES [J].

CATIVIELA, C ;

GARCIA, JI ;

MAYORAL, JA ;

SALVATELLA, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (04) :847-851

[10] Solvent effects on Diels-Alder reactions. The use of aqueous mixtures of fluorinated alcohols and the study of reactions of acrylonitrile [J].

Cativiela, C ;

Garcia, JI ;

Gil, J ;

Martinez, RM ;

Mayoral, JA ;

Salvatella, L ;

Urieta, JS ;

Mainar, AM ;

Abraham, MH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (03) :653-660

← 1 2 3 4 5 6 7 8 →