THE REACTION OF TRIS(TRIMETHYLSILYL)SILANE WITH ACID-CHLORIDES

被引：35

作者：

BALLESTRI, M

CHATGILIALOGLU, C

CARDI, N

SOMMAZZI, A

机构：

[1] CNR,LCOCEA,VIA CHIM 8,I-40064 OZZANO EMILIA,ITALY

[2] IST GUIDO DONEGANI SPA,I-28100 NOVARA,ITALY

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(00)91733-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tris(trimethylsilyl)silane, in contrast with tributyltin hydride, reduces acid chlorides to the corresponding decarboxylated hydrocarbons via a free radical mechanism. This methodology could be a viable alternative to Barton's decarboxylation reaction.

引用

收藏

页码：1787 / 1790

页数：4

相关论文

共 24 条

[1] ADDITION OF TRIS(TRIMETHYLSILYL)SILYL RADICALS TO THE CARBONYL GROUP [J].

ALBERTI, A ;

CHATGILIALOGLU, C .

TETRAHEDRON, 1990, 46 (11) :3963-3972

[2] TRIS(TRIMETHYLSILYL)SILANE AS A RADICAL-BASED REDUCING AGENT IN SYNTHESIS [J].

BALLESTRI, M ;

CHATGILIALOGLU, C ;

CLARK, KB ;

GRILLER, D ;

GIESE, B ;

KOPPING, B .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :678-683

[3]

Barton D. H. R., 1990, ALDRICHIM ACTA, V23, P3

[4] FREE-RADICAL REACTIONS IN SOLUTION .4. RADICAL-INITIATED REDUCTION OF ACID-CHLORIDES TO ALKANES BY TRI-N-PROPYLSILANE - REMOVAL OF UNWANTED CARBOXY-GROUPS FROM ORGANIC-MOLECULES [J].

BILLINGHAM, NC ;

JACKSON, RA ;

MALEK, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (05) :1137-1141

[5]

CEKOVIC Z, 1972, TETRAHEDRON LETT, P749

[6]

CEKOVIC Z, 1981, HEM DRUS BEOGRAD, V46, P238

[7] RATE CONSTANTS AND ARRHENIUS PARAMETERS FOR THE REACTIONS OF SOME CARBON-CENTERED RADICALS WITH TRIS(TRIMETHYLSILYL)SILANE [J].

CHATGILIALOGLU, C ;

DICKHAUT, J ;

GIESE, B .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6399-6403

[8] RATE CONSTANTS FOR THE REACTIONS OF TRIS(TRIMETHYLSILYL)SILYL RADICALS WITH ORGANIC HALIDES [J].

CHATGILIALOGLU, C ;

GRILLER, D ;

LESAGE, M .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2492-2494

[9]

CHATGILIALOGLU C, IN PRESS ACC CHEM RE

[10] RATE CONSTANTS FOR SOME PROTOTYPE RADICAL REACTIONS IN LIQUIDS BY KINETIC ELECTRON-SPIN-RESONANCE [J].

FISCHER, H ;

PAUL, H .

ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (05) :200-206