HYDROACYLATION OF ALKYL VINYL KETONES AND ACRYLIC ESTERS USING ORGANOTETRACARBONYLFERRATES - SYNTHESIS OF 1,4-DICARBONYL COMPOUNDS

被引：20

作者：

YAMASHITA, M

TASHIKA, H

UCHIDA, M

机构：

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1992年 / 65卷 / 05期

关键词：

D O I：

10.1246/bcsj.65.1257

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkyl vinyl ketones and acrylic esters were hydroacylated with organotetracarbonylferrates to the corresponding 1,4-diketones and 4-oxo carboxylic acid derivatives in good yield in dipolar aprotic solvents such as N,N-dimethylacetamide. Addition of 18-crown-6-improved the yield. cis-Jasmone and gamma-jasmolactone were synthesized by use of these reactions.

引用

收藏

页码：1257 / 1261

页数：5

相关论文

共 18 条

[1] DICHOTOMOUS REACTIONS OF THIOKETONES WITH TETRACARBONYLFERRATE [J].

ALPER, H ;

MARCHAND, B ;

TANAKA, M .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (05) :598-600

[2]

BROWN JM, 1979, COMPREHENSIVE ORGANI, V2, P790

[3] LOW-TEMPERATURES FAVOR KINETIC 1,4-ADDITION OVER 1,2-ADDITION OF ORGANOLITHIUMS TO ALPHA-ENONES - THE CRUCIAL ROLE OF ION-PAIRING [J].

COHEN, T ;

ABRAHAM, WD ;

MYERS, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7923-7924

[4] DISODIUM TETRACARBONYLFERRATE - TRANSITION-METAL ANALOG OF A GRIGNARD-REAGENT [J].

COLLMAN, JP .

ACCOUNTS OF CHEMICAL RESEARCH, 1975, 8 (10) :342-347

[5] HYDROACYLATION OF MICHAEL ACCEPTORS THROUGH SEQUENTIAL INSERTION REACTIONS OF ORGANOTETRACARBONYLFERRATES [J].

COOKE, MP ;

PARLMAN, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) :5222-5224

[6] A METHOD FOR 1,4 ADDITION OF ACYL GROUPS TO CONJUGATED ENONES [J].

COREY, EJ ;

HEGEDUS, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (17) :4926-&

[7]

FINKE RG, 1988, ORG SYNTH, V6, P807

[8] ONE-FLASK PREPARATION OF ANALYTICALLY PURE K2FE(CO)4 [J].

GLADYSZ, JA ;

TAM, W .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (11) :2279-2280

[9] (PHOSPHINE)CARBONYLNITROSYLACYLCOBALTATE COMPLEXES AS ACYL TRANSFER REAGENTS - ACYLATION OF ALLYLIC HALIDES, CONJUGATED ENONES, AND QUINONES [J].

HEGEDUS, LS ;

PERRY, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24) :4955-4960

[10]

Ho, 1988, CARBOCYCLE CONSTRUCT