Scope and limitations of lithium-ethylenediamine-THF-mediated cleavage at the α-position of aromatics:: Deprotection of aryl methyl ethers and benzyl ethers under mild conditions

被引：8
|
作者：
Shindo, T [1 ]
Fukuyama, Y [1 ]
Sugai, T [1 ]
机构：
[1] Keio Univ, Dept Chem, Yokohama, Kanagawa 2238522, Japan
来源：
SYNTHESIS-STUTTGART | 2004年 / 05期
关键词：
electron transfer; ethers; lithium; phenols; protective groups;
D O I：
10.1055/s-2004-815977
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The scope and limitation of lithium-ethylenediamine-THF-mediated reductive bond cleavage at the alpha-position of aromatics were examined. Very mild conditions such as lithium metal (5 equiv) and ethylenediamine (7 equiv) in oxygen-free THF were quite effective for the demethylation of aromatic ethers even at as low as -10 degreesC. Allyl benzyl ethers were also deprotected under these conditions with very little change of the allylic alcohol moiety. Through this study, 2,6-dimethylbenzyl (m-xylylmethyl, MXM) group was developed as an alternative of benzyl group, which is readily cleavable under the above mentioned reductive conditions.
引用
收藏
页码：692 / 700
页数：9
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