RING-OPENING OF A FATTY EPOXIDE BY DIETHYLACETAMIDO MALONATE IN BASIC-MEDIUM BY PHASE-TRANSFER CATALYSIS OR UNDER MICROWAVE IRRADIATION

被引：12

作者：

ABENHAIM, D ^{[1
]}

LOUPY, A ^{[1
]}

MAHIEU, C ^{[1
]}

SEMERIA, D ^{[1
]}

机构：

[1] LOREAL SA,F-93601 AULNAY SOUS BOIS,FRANCE

来源：

SYNTHETIC COMMUNICATIONS | 1994年 / 24卷 / 13期

关键词：

D O I：

10.1080/00397919408010188

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fatty epoxide (tetradecyl-oxirane) is reacted with diethyl acetamidomalonate in basic medium, with or without solvent under solid-liquid phase transfer catalysis with LiCl, or under microwave irradiation on supported reagents (KF/Al2O3/LiCl). The main product is a lactone which is formed after epoxide ring opening and subsequent cyclisation. We put here into evidence, for the first time, the conjugated advantages of ''dry media'' reactions, lithium salt effects and microwave irradiation.

引用

页码：1809 / 1816

页数：8

共 22 条

[1] BERGER A, 1973, HELV CHIM ACTA, V56, P1838
[2] EASY MICHAEL ADDITION BY SOLID-LIQUID PHASE-TRANSFER CATALYSIS ABNORMAL REACTION OF N-ACETYLAMINOMALONATE
BRAM, G
SANSOULET, J
GALONS, H
MIOCQUE, M
[J]. SYNTHETIC COMMUNICATIONS, 1988, 18 (04) : 367 - 380
[3] BRAM G, 1992, SOLID SUPPORTS CATAL, pCH12
[4] BRAM G, 1987, PHARMAZIE, V42, P34
[5] SPECIFIC CATION PARTICIPATION IN ALKALI-CARBANION INITIATED EPOXIDE CLEAVAGE REACTIONS
CHANG, CJ
KIESEL, RF
HOGENESC.TE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (25) : 8446 - 8448
[6] CHII M, 1992, TETRAHEDRON, V48, P3805
[7] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .4. SYNTHESIS AND REACTIONS OF THE CIS-OXIDES AND TRANS-OXIDES DERIVED FROM 3-[(BENZYLOXY)METHYL]CYCLOHEXENE
CHINI, M
CROTTI, P
FLIPPIN, LA
GARDELLI, C
MACCHIA, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) : 1713 - 1718
[8] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .5. SYNTHESIS AND REACTIONS OF SOME 2,3-EPOXY-1-ALKANOL DERIVATIVES
CHINI, M
CROTTI, P
FLIPPIN, LA
GARDELLI, C
GIOVANI, E
MACCHIA, F
PINESCHI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) : 1221 - 1227
[9] FOUCAUD A, 1987, PREPARATIVE CHEM USI, pCH17
[10] ORGANIC-REACTIONS WITHOUT SOLVENT - MICHAEL ADDITIONS ON AN UNSATURATED SULFONE AND SULFOXIDE
GALONS, H
LABIDALLE, S
MIOCQUE, M
LIGNIERE, B
BRAM, G
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1988, 39 (1-2): : 73 - 78

← 1 2 3 →