CATALYTIC HYDROGENOLYSIS OF CYCLOPROPANES - METAL INSERTION INTO A SATURATED CARBON-CARBON BOND AS THE KEY STEP

被引：7

作者：

BESSARD, Y ^{[1
]}

SCHLOSSER, M ^{[1
]}

机构：

[1] UNIV LAUSANNE,INST CHIM ORGAN,RUE BARRE 2,CH-1005 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 07期

关键词：

D O I：

10.1016/S0040-4020(01)86379-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrogenolytic ring cleavage of gem-difluorocyclopropanes occurs exclusively at the carbon-carbon bond opposite to the halogen-bearing center and affords mainly gem-difluoroalkanes. The intermediacy of catalyst/cyclopropane derived adducts (e.g., palladacyclobutanes or 1,3-dipalladiopropanes) is postulated in order to rationalize the formation of monofluorinated and halogen-free by-products and, in addition, to explain specific substituent effects on the reaction rates.

引用

页码：1231 / 1238

页数：8

共 39 条

[1] STEREOCHEMISTRY OF PALLADIUM(II)-INDUCED RING-OPENING OF THE CYCLOPROPANE IN A VINYLCYCLOPROPANE - CHLOROPALLADATION OF CAR-2-ENE [J].

AHMAD, MU ;

BACKVALL, JE ;

NORDBERG, RE ;

NORIN, T ;

STROMBERG, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (05) :321-323

[2] HYBRIDIZATION EFFECTS IN FLUOROCARBONS [J].

BERNETT, WA .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06) :1772-&

[3]

BESSARD Y, 1990, IN PRESS TETRAHEDRON, V46

[4]

BINGER P, 1973, SYNTHESIS-STUTTGART, P427

[5] REACTIONS OF METHYLENECYCLOPROPANE .4. PALLADIUM(0)-CATALYZED CODIMERIZATION OF METHYLENECYCLOPROPANE WITH ALKENES [J].

BINGER, P ;

SCHUCHARDT, U .

CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (10) :3334-3341

[6] EFFECT OF SUCCESSIVE FLUORINATION ON THE STRUCTURE OF CYCLOPROPANE [J].

BOGGS, JE ;

FAN, K .

ACTA CHEMICA SCANDINAVICA SERIES A-PHYSICAL AND INORGANIC CHEMISTRY, 1988, 42 (8-9) :595-602

[7] THE MOLECULAR STRUCTURES OF NORMAL-PENTANE, NORMAL-HEXANE AND NORMAL-HEPTANE [J].

BONHAM, RA ;

BARTELL, LS ;

KOHL, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (18) :4765-4769

[8]

Boswell G. A., 1974, ORG REACTIONS, V21, P1

[9]

BUNGE W, 1959, HOUBENWEYL METHODEN, V1, P814

[10] BROMODIFLUOROMETHYLPHOSPHONIUM SALTS - CONVENIENT SOURCE OF DIFLUOROCARBENE [J].

BURTON, DJ ;

NAAE, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (25) :8467-8468

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