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.
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收藏
页码：2411 / 2424
页数：14
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