LICLO4 IN ETHER - AN UNUSUAL SOLVENT

被引：74

作者：

WALDMANN, H

机构：

[1] Institut Für Organische Chemie Und Biochemie, Universität Bonn, W-5300

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 10期

关键词：

D O I：

10.1002/anie.199113061

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ionic reactions with polarized transition states are favored by the solvent system LiClO4/Et2O (3-5M). This is demonstrated by (hetero)Diels-Alder reactions and by the sigmatropic rearrangement of allyl vinyl ethers in this medium. The former react even faster and with higher endo selectivity than in water; the latter are not [3,3] but [1,3] sigmatropic rearrangements, which yield aldehydes. An important advantage of the LiClO4/Et2O system is it that may also be used for acceleration of reactions sensitive to hydrolysis.

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页码：1306 / 1308

页数：3

相关论文

共 23 条

[1] THE POLARITY OF SOLUTIONS OF LITHIUM PERCHLORATE IN WATERFREE ETHERS [J].

BRAUN, R ;

SAUER, J .

CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (04) :1269-1274

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

BRESLOW, R ;

MAITRA, U .

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

[3]

BRESLOW R, 1991, ACCOUNTS CHEM RES, V24, P150

[4] SIMPLE, EFFICIENT TOTAL SYNTHESIS OF CANTHARIDIN VIA A HIGH-PRESSURE DIELS-ALDER REACTION [J].

DAUBEN, WG ;

KESSEL, CR ;

TAKEMURA, KH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (22) :6893-6894

[5]

Diels O, 1931, LIEBIGS ANN CHEM, V490, P243

[6]

FOHLISCH B, 1988, CHEM BER-RECL, V121, P1585

[7] WATER AS A SOLVENT FOR THE CLAISEN REARRANGEMENT - PRACTICAL IMPLICATIONS FOR SYNTHETIC ORGANIC-CHEMISTRY [J].

GRIECO, PA ;

BRANDES, EB ;

MCCANN, S ;

CLARK, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5849-5851

[8] [1,3] SIGMATROPIC REARRANGEMENT OF ALLYL VINYL ETHERS AT AMBIENT-TEMPERATURE IN 3.0M LITHIUM PERCHLORATE-DIETHYL ETHER [J].

GRIECO, PA ;

CLARK, JD ;

JAGOE, CT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5488-5489

[9] DRAMATIC RATE ACCELERATIONS OF DIELS-ALDER REACTIONS IN 5-M LITHIUM PERCHLORATE DIETHYL-ETHER - THE CANTHARIDIN PROBLEM REEXAMINED [J].

GRIECO, PA ;

NUNES, JJ ;

GAUL, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4595-4596

[10] AQUEOUS INTERMOLECULAR DIELS-ALDER CHEMISTRY - REACTION OF (E)-2,4-PENTADIENYL AMMONIUM-CHLORIDE AND RELATED AMMONIUM-SALTS WITH DIENOPHILES IN WATER [J].

GRIECO, PA ;

GALATSIS, P ;

SPOHN, RF .

TETRAHEDRON, 1986, 42 (11) :2847-2853