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.

引用

收藏

页码：5163 / 5165

页数：3

相关论文

共 41 条

[31] HIGH-YIELD ACYL ANION TRANSFER-REACTIONS - NUCLEOPHILIC ACYLATION OF ALDEHYDES [J].

SEYFERTH, D ;

WEINSTEIN, RM ;

WANG, WL ;

HUI, RC .

TETRAHEDRON LETTERS, 1983, 24 (45) :4907-4910

[32] HIGH-YIELD ACYL ANION TRAPPING REACTIONS - DIRECT NUCLEOPHILIC ACYLATION OF ISOCYANATES AND ISOTHIOCYANATES [J].

SEYFERTH, D ;

HUI, RC .

TETRAHEDRON LETTERS, 1984, 25 (46) :5251-5254

[33] AROYL ANION TRAPPING REACTIONS - A PRELIMINARY-STUDY OF DIRECT NUCLEOPHILIC AROYLATION BY MEANS OF LOW-TEMPERATURE, INSITU (CH3)NC6H5NLI/CO SYSTEMS [J].

SEYFERTH, D ;

WANG, WL ;

HUI, RC .

TETRAHEDRON LETTERS, 1984, 25 (16) :1651-1654

[34] SYNTHESIS OF ALPHA-DIKETONES BY DIRECT, LOW-TEMPERATURE, INSITU NUCLEOPHILIC ACYLATION OF ESTERS BY ACYLLITHIUM REAGENTS [J].

SEYFERTH, D ;

WEINSTEIN, RM ;

HUI, RC ;

WANG, WL ;

ARCHER, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5768-5773

[35] REACTIONS OF INSITU GENERATED ACYLLITHIUM REAGENTS WITH CARBON-DISULFIDE AND CARBONYL SULFIDE [J].

SEYFERTH, D ;

HUI, RC .

TETRAHEDRON LETTERS, 1984, 25 (25) :2623-2626

[36] PREPARATION OF ALPHA-OXO AMIDINES BY THE DIRECT NUCLEOPHILIC ACYLATION OF CARBODIIMIDES [J].

SEYFERTH, D ;

HUI, RC .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11) :1985-1987

[37]

SEYFERTH D, 1983, J ORG CHEM, V48, P114

[38] REINVESTIGATION OF PREPARATION OF BORYLKETONES (ACYLDIALKYLBORANES) [J].

SMITH, K ;

SWAMINATHAN, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (17) :719-720

[39] HYDROBORATION .84. CONTROLLED AND SEQUENTIAL HYDROBORATION OF SIMPLE REPRESENTATIVE ALKENES WITH MONOORGANYLBORANES IN TETRAHYDROFURAN - A CONVENIENT SYNTHESIS OF MIXED BORINIC ESTERS, R1R2BOR3, AND MIXED TRIALKYLBORANES, R1R2R3B - AN EXAMINATION OF POSITIONAL SELECTIVITY IN THE 1ST AND 2ND STATES OF HYDROBORATION [J].

SREBNIK, M ;

COLE, TE ;

RAMACHANDRAN, PV ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6085-6096

[40] COLORED INDICATORS FOR SIMPLE DIRECT TITRATION OF MAGNESIUM AND LITHIUM REAGENTS [J].

WATSON, SC ;

EASTHAM, JF .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 9 (01) :165-&

← 1 2 3 4 5 →