ENOLIC RADICAL DERIVED FROM ACETIC-ACID - A USEFUL RADICAL ALTERNATIVE TO ACETATE ENOLATE IN MICHAEL-TYPE REACTIONS

被引：16

作者：

FOUBELO, F ^{[1
]}

LLORET, F ^{[1
]}

YUS, M ^{[1
]}

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,APDO 99,E-03080 ALICANTE,SPAIN

来源：

TETRAHEDRON | 1993年 / 49卷 / 37期

关键词：

D O I：

10.1016/S0040-4020(01)81929-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of iodoacetic acid 1 with tributyltin chloride and sodium borohydride in the presence of different electrophilic olefins 2 (methyl, allyl or tert-butyl acrylates, N,N-dimethyl or N,N-di-iso-propyl acrylamides, acrylonitrile, methyl methacrylate, methacrylonitrile and 1,1-dichloroethylene) and AIBN as an initiator yields, after treatment with aqueous sodium fluoride, the corresponding products 3 through a radical Michael-type process.

引用

页码：8465 / 8470

页数：6

共 21 条

[1] FREE-RADICAL REACTIONS OF ORGANOMERCURIALS [J].

BARLUENGA, J ;

YUS, M .

CHEMICAL REVIEWS, 1988, 88 (03) :487-509

[2] PROTOTROPIC REARRANGEMENT OF SECONDARY PROPARGYLIC AMINES [J].

BENEFRAIM, DA .

TETRAHEDRON, 1973, 29 (24) :4111-4125

[3] ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS [J].

CHATGILIALOGLU, C .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) :188-194

[4]

CUSHMAN DW, 1977, Patent No. 2704985

[5] HOMOENOLIC RADICAL DERIVED FROM PROPIONIC-ACID - A VERSATILE REAGENT FOR THE RADICAL VERSION OF THE MICHAEL REACTION [J].

FOUBELO, F ;

LLORET, F ;

YUS, M .

TETRAHEDRON, 1992, 48 (43) :9531-9536

[6] SYNTHESES WITH RADICALS-C-C BOND FORMATION VIA ORGANOTIN AND ORGANOMERCURY COMPOUNDS [J].

GIESE, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (07) :553-565

[7] OXIDATION BY METAL SALTS .4. A NEW METHOD FOR PREPARATION OF GAMMA-LACTONES BY REACTION OF MANGANIC ACETATE WITH OLEFINS [J].

HEIBA, EI ;

DESSAU, RM ;

KOEHL, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (21) :5905-&

[8] OXIDATION BY METAL-SALTS .10. ONE-STEP SYNTHESIS OF GAMMA-LACTONES FROM OLEFINS [J].

HEIBA, EI ;

DESSAU, RM ;

RODEWALD, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (26) :7977-7981

[9] APPROACHES TO SYNTHESIS OF INSECT JUVENILE-HORMONE ANALOG ETHYL "3,7,11-TRIMETHYL-2,4-DODECADIENOATE AND ITS PHOTOCHEMISTRY [J].

HENRICK, CA ;

WILLY, WE ;

MCKEAN, DR ;

BAGGIOLINI, E ;

SIDDALL, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (01) :8-14

[10] STANNYL ESTER CYCLIZATIONS [J].

KRAUS, GA ;

LANDGREBE, K .

TETRAHEDRON, 1985, 41 (19) :4039-4046

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