Rate enhancement of Diels-Alder reactions in aqueous perfluorinated emulsions

被引：17

作者：

Nishimoto, Kohsuke ^{[1
]}

Kim, Shokaku ^{[1
]}

Kitano, Yoshikazu ^{[1
]}

Tada, Masahiro ^{[1
]}

Chiba, Kazuhiro ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Bioorgan Chem Lab, Fuchu, Tokyo 1838509, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 24期

关键词：

D O I：

10.1021/ol0623116

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A marked acceleration property for the Diels-Alder reaction was observed in an aqueous micellar system composed of perfluorohexane and lithium perfluorooctanesulfonate. The reaction rate increased with the concentration of the equimolar mixture of PFH and LiFOS, and the rate in 500 mM PFH and 500 mM LiFOS was about 100-fold greater than that in water without the fluorous field. After completion of the reaction, the products were simply extracted from the aqueous reaction mixture using n-hexane.

引用

页码：5545 / 5547

页数：3

共 22 条

[1] 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

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

BRESLOW, R .

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

[3] EXPERIMENTAL AND THEORETICAL-STUDY OF THE INFLUENCE OF THE SOLVENT ON ASYMMETRIC DIELS-ALDER REACTIONS [J].

CATIVIELA, C ;

GARCIA, JI ;

MAYORAL, JA ;

ROYO, AJ ;

SALVATELLA, L ;

ASSFELD, X ;

RUIZLOPEZ, MF .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1992, 5 (05) :230-238

[4] Accelerated Diels-Alder reaction of quinones generated in situ by a modified electrode in an aqueous sodium dodecyl sulfate micellar system [J].

Chiba, K ;

Jinno, M ;

Nozaki, A ;

Tada, M .

CHEMICAL COMMUNICATIONS, 1997, (15) :1403-1404

[5] Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines [J].

Curran, DP ;

Wang, XA ;

Zhang, QS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3716-3719

[6]

Curran DP, 1998, ANGEW CHEM INT EDIT, V37, P1175, DOI 10.1002/(SICI)1521-3773(19980518)37:9<1174::AID-ANIE1174>3.0.CO

[7]

2-P

[8]

CURRAN DP, 2004, J ORG CHEM, P128

[9] A SEMITHEORETICAL MULTIPARAMETER APPROACH TO CORRELATE SOLVENT EFFECTS ON REACTIONS AND EQUILIBRIA [J].

GAJEWSKI, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) :5500-5506

[10]

Grieco P.A., 1998, Organic synthesis in water

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