1,2-ELIMINATION OF ALCOHOL FROM HOMOALLYL ETHERS UNDER THE INFLUENCE OF MIXED METAL BASES

被引：45

作者：

MARGOT, C ^{[1
]}

RIZZOLIO, M ^{[1
]}

SCHLOSSER, M ^{[1
]}

机构：

[1] UNIV LAUSANNE,INST CHIM ORGAN,RUE DE LA BARRE 2,CH-1005 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 07期

关键词：

D O I：

10.1016/S0040-4020(01)82022-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithium diisopropylamide in the presence of catalytic amounts of potassium tert-butoxide smoothly converts homoallyl or homobenzyl type ethers to dienes e.g.e.g., 1,3,5,26 or styrenes (2). γ,δ-Unsaturated acetals give 13-dienyl ethers e.g., 4 and 4-alkylidenetetrahydropyrans or dihydropyrans produce a variety of dienols (e.g., 6-17,20-22). - If there is a choice, the new double bond is formed with high trans-selectivity while the configuration of existing double bonds is retained. - The elimination mode is syn-periplanar and concerted, though E1cb like. © 1990.

引用

页码：2411 / 2424

页数：14