Organometallic reactions in aqueous media - Antimony-mediated allylation of carbonyl compounds and the nature of allylstibine intermediates

被引：10

作者：

Li, LH ^{[1
]}

Chan, TH ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2001年 / 79卷 / 11期

关键词：

allylation reaction; aqueous organometallic reactions; homoallylic alcohols; allylstibine dibromide; diallylstibine bromide;

D O I：

10.1139/cjc-79-11-1536

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Commercial antimony metal, in aqueous 1 M H(D)Cl solution, reacts with allyl bromide and aldehydes to give the corresponding homoallylic alcohols in good yield. The reaction proceeds through the formation of allylstibine intermediates. The structures of the allylstibine intermediates are likely to be allylstibine dibromide and diallylstibine bromide.

引用

收藏

页码：1536 / 1540

页数：5

相关论文

共 37 条

[1] CADMIUM METAL-MEDIATED ALLYLATION OF CARBONYL-COMPOUNDS [J].

ARAKI, S ;

ITO, H ;

BUTSUGAN, Y .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 347 (1-2) :5-9

[2]

Barbier P., 1899, CR HEBD ACAD SCI, V128, P110

[3]

Blomberg C., 1993, REACTIVITY STRUCTURE

[4] BARBIER-GRIGNARD-TYPE ALLYLATION OF ALDEHYDES WITH METALLIC ANTIMONY [J].

BUTSUGAN, Y ;

ITO, H ;

ARAKI, S .

TETRAHEDRON LETTERS, 1987, 28 (32) :3707-3708

[5] Organometallic reactions in aqueous media. The nature of the organotin intermediate in the tin-mediated allylation of carbonyl compounds [J].

Chan, TH ;

Yang, Y ;

Li, CJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4452-4455

[6] Indium-mediated organometallic reactions in aqueous media: The nature of the allylindium intermediate [J].

Chan, TH ;

Yang, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3228-3229

[7] 1993 RU-LEMIEUX-AWARD-LECTURE - ORGANOMETALLIC-TYPE REACTIONS IN AQUEOUS-MEDIA - A NEW CHALLENGE IN ORGANIC-SYNTHESIS [J].

CHAN, TH ;

LI, CJ ;

LEE, MC ;

WEI, ZY .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05) :1181-1192

[8] Organometallic-type reactions in aqueous media mediated by indium: Application to the synthesis of carbohydrates [J].

Chan, TH ;

Isaac, MB .

PURE AND APPLIED CHEMISTRY, 1996, 68 (04) :919-924

[9] SELECTIVE ALLYLATION OF CARBONYL-COMPOUNDS IN AQUEOUS-MEDIA [J].

EINHORN, C ;

LUCHE, JL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 322 (02) :177-183

[10] REDUCTIVE VINYLATION-ALPHA TO KETONES [J].

KOWALSKI, CJ ;

DUNG, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (27) :7950-7951

← 1 2 3 4 →