EVIDENCE FOR THE FORMATION OF ACYLBORONATE INTERMEDIATES IN THE CARBONYLATION REACTIONS OF ORGANOBORANES

被引：26

作者：

KABALKA, GW ^{[1
]}

GOTSICK, JT ^{[1
]}

PACE, RD ^{[1
]}

LI, NS ^{[1
]}

机构：

[1] UNIV TENNESSEE,DEPT RADIOL,KNOXVILLE,TN 37996

来源：

ORGANOMETALLICS | 1994年 / 13卷 / 12期

关键词：

D O I：

10.1021/om00024a069

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Trialkylboranes react with acyllithium reagents to yield ketones after oxidation with hydrogen peroxide. The ketones contain one alkyl group supplied by the alkyllithium reagent and one alkyl group supplied by the organoborane. The experimental results support the hypothesis that an acylboronate is an intermediate in the reactions of organoboranes with carbon monoxide. The yields are modest due to an apparent competition between carbon monoxide and organoborane for the alkyllithium needed to generate the acyl anion.

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页码：5163 / 5165

页数：3

相关论文

共 41 条

[1]

Brown H. C., 1968, J CHEM SOC CHEM COMM, P594

[2] REACTION OF CARBON MONOXIDE AT ATMOSPHERIC PRESSURE WITH TRIALKYLBORANES . A CONVENIENT SYNTHESIS OF TRIALKYLCARBINOLS VIA HYDROBORATION [J].

BROWN, HC ;

RATHKE, MW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (11) :2737-&

[3] CONVERSION OF LINEAR TRIENES INTO BICYCLIC BORANES VIA HYDROBORATION-ISOMERIZATION AND THEIR CARBONYLATION . A SIMPLE SYNTHESIS OF ANGULARLY SUBSTITUTED BICYCLIC ALCOHOLS [J].

BROWN, HC ;

NEGISHI, EI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (05) :1224-&

[4] HYDROBORATION .70. THE POLYCYCLIC HYDROBORATION OF ACYCLIC AND CYCLIC TRIENES WITH BORANE IN TETRAHYDROFURAN AND TRIETHYLAMINE-BORANE - REEXAMINATION OF THE STEREOCHEMISTRY OF ISOMERIC PERHYDRO-9B-BORAPHENALENES [J].

BROWN, HC ;

NEGISHI, E ;

DICKASON, WC .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (04) :520-527

[5] ORGANOBORANE-CARBON MONOXIDE REACTIONS . A NEW VERSATILE APPROACH TO SYNTHESIS OF CARBON STRUCTURES [J].

BROWN, HC .

ACCOUNTS OF CHEMICAL RESEARCH, 1969, 2 (03) :65-&

[6] TRIALKYLBORANE-INDUCED REACTION OF CARBON-MONOXIDE WITH ALKALI-METAL TRIALKYLBOROHYDRIDES - REMARKABLE CORRELATION OF B-11 NUCLEAR MAGNETIC-RESONANCE SPECTRA WITH REACTIVITY [J].

BROWN, HC ;

HUBBARD, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (03) :467-468

[7] HOMOLOGATION OF ORGANOBORANES VIA CARBONYLATION-REDUCTION [J].

BROWN, HC ;

FORD, TM ;

HUBBARD, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (20) :4067-4068

[8] CARBONYLATION OF THEXYLDIALKYLBORANES . A NEW GENERAL SYNTHESIS OF KETONES [J].

BROWN, HC ;

NEGISHI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) :5285-&

[9] CARBONYLATION OF ORGANOBORANES FROM CYCLIC HYDROBORATION OF DIENES WITH THEXYLBORANE . A SIMPLE PROCEDURE FOR CONVERSION OF DIENES INTO CYCLIC KETONES [J].

BROWN, HC ;

NEGISHI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) :5477-&

[10] CARBONYLATION OF MIXED TRIALKYLBORANES . EVIDENCE FOR INTRAMOLECULAR NATURE OF TRANSFER OF GROUPS FROM BORON TO CARBON IN CARBONYLATION REACTION . A CONVENIENT SYNTHESIS OF UNSYMMETRICAL KETONES RR'CO [J].

BROWN, HC ;

RATHKE, MW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4528-&

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