Highly stereoselective synthesis of conjugated polyenes via a homocoupling reaction of unsaturated silanes

被引：56

作者：

Babudri, F ^{[1
]}

Cicciomessere, AR ^{[1
]}

Farinola, GM ^{[1
]}

Fiandanese, V ^{[1
]}

Marchese, G ^{[1
]}

Musio, R ^{[1
]}

Naso, F ^{[1
]}

Sciacovelli, O ^{[1
]}

机构：

[1] UNIV BARI,DIPARTMENTO CHIM,CTR CNR STUDIO METODOL INNOVAT SINTESI ORGAN,I-70126 BARI,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 10期

关键词：

D O I：

10.1021/jo9700437

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the synthesis of conjugated polyenes containing up to eight double bonds with all-E configuration is reported. The procedure is based upon a homocoupling reaction of dienyl-, trienyl-, or tetraenylsilanes, promoted by PdCl2 in methanol and in the presence of LiCl and CuCl2. Configurational and conformational assignments were rigorously made on the basis of NMR spectra. The compounds obtained represent a novel interesting class of symmetrically substituted polyenes with potential optical and electrooptical properties. By changing the solvent, the homocoupling process can be switched to the halogenation of the silyl-substituted terminal double bond, thus leading to polyenyl halides.

引用

页码：3291 / 3298

页数：8

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