ALKYLATION OF HETEROARYL ALKYL METALS BY BISTRIALKYLSILYLPEROXIDES

被引：13

作者：

EPIFANI, E ^{[1
]}

FLORIO, S ^{[1
]}

TROISI, L ^{[1
]}

机构：

[1] UNIV LECCE,DEPARTIMENTO BIOL,CHIM ORGAN LAB,VIA MONTERONI,I-73100 LECCE,ITALY

来源：

TETRAHEDRON | 1990年 / 46卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(01)90538-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heteroaryl alkyl metals 3 undergo methylation and ethylation upon treatment with bistrimethylsilylperoxide la and bistriethylsilylperoxide 1b. Benzothiazolylderivatives 3c-d and 3h-j react with la giving trimethylsilyloxylation other than methylation products. The reaction of 3a-b with la leads also to the trimethylsilylation product 1. The reaction of 3g, 3c and 3k with 1b provides the ethylated derivatives 2h, 2d and 2n respectively. No reaction occurred when 3c was treated with lc. © 1990.

引用

页码：4031 / 4038

页数：8

共 15 条

[1] BIS(TRIMETHYLSILYL) MONO-PEROXYSULFATE - CONVENIENT BAEYER-VILLIGER OXIDANT [J].

ADAM, W ;

RODRIGUEZ, A .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (26) :4969-4970

[2] PEROXO COMPOUNDS .12. NON-RADICAL REACTIONS OF BIS(TRIMETHYLSILYL)PEROXIDE [J].

BRANDES, D ;

BLASCHET.A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 73 (02) :217-227

[3] PEROXO COMPOUNDS .11. NON-RADICAL SUBSTITUTION AND REDOX REACTIONS OF BIS(TRIMETHYLSILYL)PEROXIDE [J].

BRANDES, D ;

BLASCHET.A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 49 (01) :C6-C8

[4]

Colvin E. W., 1981, SILICON ORGANIC SYNT

[5] 1,4-DIAZA[2.2.2]BICYCLOOCTANE-HYDROGEN PEROXIDE COMPLEX AS A SOURCE OF ANHYDROUS HYDROGEN-PEROXIDE - PREPARATION OF BIS(TRIALKYLSILYL) PEROXIDES [J].

COOKSON, PG ;

DAVIES, AG ;

FAZAL, N .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 99 (02) :C31-C32

[6] ON THE REACTIVITY OF SILYLPEROXIDES - OXIDATION OF THIOXANE AND OF N,N-DIMETHYL-PARA-ANISIDINE BY BIS(TRIMETHYLSILYL)PEROXIDE AND BY TERT-BUTYL(TRIMETHYLSILYL)PEROXIDE [J].

CURCI, R ;

MELLO, R ;

TROISI, L .

TETRAHEDRON, 1986, 42 (03) :877-883

[7] REVERSIBLE ALLYLIC CONDENSATION OF METALLOALLYLS OF HETEROCYCLES - COUNTERION EFFECT [J].

EPIFANI, E ;

FLORIO, S ;

INGROSSO, G .

TETRAHEDRON, 1988, 44 (18) :5869-5877

[8] REGIOSELECTIVE CONTROL OF ALLYLLITHIUMS OF SOME HETEROCYCLES - ALPHA-VS-GAMMA CONDENSATION WITH ALDEHYDES [J].

EPIFANI, E ;

FLORIO, S ;

INGROSSO, G .

TETRAHEDRON LETTERS, 1987, 28 (50) :6385-6388

[9] SOME USES OF SILICON-COMPOUNDS IN ORGANIC-SYNTHESIS [J].

FLEMING, I .

CHEMICAL SOCIETY REVIEWS, 1981, 10 (01) :83-111

[10] REACTION OF 2-HETEROSUBSTITUTED BENZOTHIAZOLES WITH ALLYLIC GRIGNARD-REAGENTS [J].

FLORIO, S ;

EPIFANI, E ;

INGROSSO, G .

TETRAHEDRON, 1984, 40 (21) :4527-4533

← 1 2 →