COPPER-CATALYZED ADDITION OF PERFLUOROALKYL IODIDES TO UNSATURATED ALCOHOLS AND TRANSFORMATION OF THE ADDITION-PRODUCTS

被引：37

作者：

KOTORA, M

HAJEK, M

AMEDURI, B

BOUTEVIN, B

机构：

[1] ACAD SCI CZECH REPUBL,INST CHEM PROC FUNDAMENTALS,ROZVOJOVA 135,CS-16502 PRAGUE 6,CZECH REPUBLIC

[2] ECOLE NATL SUPER CHIM MONTPELLIER,URA D11930,8 RUE ECOLE NORMALE,F-34053 MONTPELLIER,FRANCE

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1994年 / 68卷 / 01期

关键词：

D O I：

10.1016/0022-1139(93)02993-O

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Iodoperfluoroalkyl alcohols RFCH2CHI(CR2)nOH (RF = C6F13; R = H, CH3; n = 1-3,9) have been readily prepared in high yield by the addition of perfluoroalkyl iodides R(F)I to allylic and other unsaturated alcohols at 120-degrees-C in the presence of a catalytic amount (10% mol) of metallic copper powder. The dibenzoyl peroxide-induced reaction gave lower yields of the addition products in most cases. The chemical changes of iodoperfluoralkylated alcohols to epoxides and alcohols are described. A discussion of the by-products obtained and of the reaction mechanism is provided.

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页码：49 / 56

页数：8

相关论文

共 20 条

[1] SOME APPROACHES TO THE SYNTHESIS OF FLUORINATED ALCOHOLS AND ESTERS .2. USE OF F-ALKYL IODIDES FOR THE SYNTHESIS OF F-ALKYL ALKANOLS [J].

BRACE, NO .

JOURNAL OF FLUORINE CHEMISTRY, 1982, 20 (03) :313-327

[2]

BRACE NO, 1963, Patent No. 3083224

[3] SOLVENT EFFECTS ON THE REACTION OF 4-CHLOROOCTAFLUOROBUTYLIODIDE WITH COPPER [J].

CHEN, QY ;

YANG, ZY ;

HE, YB .

JOURNAL OF FLUORINE CHEMISTRY, 1987, 37 (02) :171-176

[4] STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION .3. PERFLUOROALKYLATION OF OLEFINS WITH PERFLUOROALKYL IODIDES AND COPPER IN VARIOUS SOLVENTS [J].

CHEN, QY ;

YANG, ZY .

JOURNAL OF FLUORINE CHEMISTRY, 1985, 28 (04) :399-411

[5] REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF BETA-HALOHYDRINS FROM 1,2-EPOXIDES WITH AMMONIUM HALIDES IN THE PRESENCE OF METAL-SALTS [J].

CHINI, M ;

CROTTI, P ;

GARDELLI, C ;

MACCHIA, F .

TETRAHEDRON, 1992, 48 (18) :3805-3812

[6] METHOD FOR CATALYTIC DEHALOGENATIONS VIA TRIALKYLTIN HYDRIDES [J].

COREY, EJ ;

SUGGS, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (17) :2554-2555

[7] TRANSITION-METAL COMPLEX CATALYZED POLYFLUOROALKYLATION - A FACILE SYNTHESIS OF FLUORINE-CONTAINING OXIRANES AND ENYNES [J].

FUCHIKAMI, T ;

SHIBATA, Y ;

URATA, H .

CHEMISTRY LETTERS, 1987, (03) :521-524

[8]

FUCHIKAMI T, 1984, TETRAHEDRON LETT, V25, P303, DOI 10.1016/S0040-4039(00)99868-X

[9] NEW EFFICIENT PALLADIUM-CATALYZED PERFLUOROALKYLATION OF CARBON-CARBON MULTIPLE BONDS WITH F-ALKYL IODIDES - AN EXPEDIENT ROUTE TO F-ALKYLATED ALKYL AND ALKENYL IODIDES [J].

ISHIHARA, T ;

KUROBOSHI, M ;

OKADA, Y .

CHEMISTRY LETTERS, 1986, (11) :1895-1896

[10] ADDITION-REACTIONS OF F-ALKYL IODIDES TO CARBON-CARBON DOUBLE-BONDS PROMOTED BY METALLIC TIN(0)-METAL SALT SYSTEMS [J].

KUROBOSHI, M ;

ISHIHARA, T .

JOURNAL OF FLUORINE CHEMISTRY, 1988, 39 (02) :299-303