Cadmium promoted allylation of acid chlorides: Synthesis of beta,gamma-unsaturated ketones

被引：25

作者：

Baruah, B ^{[1
]}

Boruah, A ^{[1
]}

Prajapati, D ^{[1
]}

Sandhu, JS ^{[1
]}

机构：

[1] REG RES LAB,JORHAT 785006,ASSAM,INDIA

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(96)02092-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and efficient method for the preparation of beta,gamma-unsaturated ketones has been achieved by a simple reaction of an acid chloride with allyl and crotyl bromide and cadmium powder in absolute tetrahydrofuran. Copyright (C) 1996 Published by Elsevier Science Ltd

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页码：9087 / 9088

页数：2

相关论文

共 22 条

[1] EQUILIBRIA BETWEEN ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED KETONES IN 6-MEMBERED RINGS FUSED BETA,GAMMA-UNSATURATED TO 5-MEMBERED, 6-MEMBERED AND 7-MEMBERED RINGS [J].

AUMILLER, JC ;

WHITTLE, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (18) :2959-2962

[2] SCOPE AND MECHANISM OF THE REACTION OF OLEFINS WITH ANHYDRIDES AND ZINC-CHLORIDE TO GIVE BETA,GAMMA-UNSATURATED KETONES [J].

BEAK, P ;

BERGER, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (11) :3848-3856

[3] A CONVENIENT SYNTHESIS OF BETA,GAMMA-UNSATURATED KETONES VIA ALLYLATION OF Z-1-HALO-1-ALKENYL-1,3,2-DIOXABOROLANE [J].

BROWN, HC ;

SOUNDARARAJAN, R .

TETRAHEDRON LETTERS, 1994, 35 (38) :6963-6966

[4] ORGANOMANGANESE(II) REAGENTS .19. ACYLATION OF ORGANOMANGANESE CHLORIDES BY CARBOXYLIC-ACID CHLORIDES IN THF - A CLEAR IMPROVEMENT IN THE FIELD OF THE PREPARATION OF KETONES FROM ORGANOMANGANESE COMPOUNDS [J].

CAHIEZ, G ;

LABOUE, B .

TETRAHEDRON LETTERS, 1989, 30 (52) :7369-7372

[5]

CURRAN DP, 1986, SYNTHESIS-STUTTGART, P312

[6] OPTICALLY-ACTIVE ALLYLSILANES .1. PREPARATION BY PALLADIUM-CATALYZED ASYMMETRIC GRIGNARD CROSS-COUPLING AND ANTI STEREOCHEMISTRY IN ELECTROPHILIC SUBSTITUTION-REACTIONS [J].

HAYASHI, T ;

KONISHI, M ;

ITO, H ;

KUMADA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (18) :4962-4963

[7] ALKYLATION OF ACID-CHLORIDES BY ALKYLRHODIUM(I) COMPLEXES [J].

HEGEDUS, LS ;

KENDALL, PM ;

LO, SM ;

SHEATS, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (19) :5448-5452

[8] ACYLATION OF OLEFINS BY ACETYL HEXACHLOROANTIMONATE - SELECTIVE FORMATION OF BETA,GAMMA-UNSATURATED KETONES UNDER KINETIC CONTROL AND MECHANISTIC RATIONALE AS AN ENE REACTION [J].

HOFFMANN, HMR ;

TSUSHIMA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (18) :6008-6011

[9]

HOSOMO A, 1978, J ORG CHEM, V43, P2251

[10] ACYLDEMETALLATION OF TITANIUM(III) PI-ALLYLIC COMPLEXES [J].

KASATKIN, AN ;

KULAK, AN ;

TOLSTIKOV, GA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 346 (01) :23-34