ALPHA-ALKOXY KETONES FROM THE NUCLEOPHILIC-SUBSTITUTION ON THE PEROXIDE BOND OF 3,3-DISUBSTITUTED 1,2-DIOXETANES BY ENAMINES

被引：10
|
作者：
ADAM, W
ANDLER, S
HEIL, M
VOERCKEL, V
机构：
[1] Institute of Organic Chemistry, University of Wurzburg, D-8700 Würzburg, Am Hubland
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 09期
关键词：
D O I：
10.1021/jo00035a025
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of 1,2-dioxetanes with enamines as pi-nucleophiles was investigated. 3,3-Dibenzyl-1,2-dioxetane (1) was allowed to react with enamines 2a-c in methylene chloride to afford after hydrolysis the corresponding alpha-alkoxylated ketones 4a-c. Additionally, the reaction of the dimedone-derived enamine 3 with dioxetane 1 yielded the oxidized enamine adduct 4. Nucleophilic attack of the enamine beta-carbon (S(N)2 reactivity) on the sterically less hindered site of the dioxetane peroxide bond is proposed to constitute the initial step of the reaction.
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页码：2680 / 2682
页数：3
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