Facile O-deallylation of allyl ethers via SN2′ reaction with tert-butyllithium

被引：41

作者：

Bailey, WF

England, MD

Mealy, MJ

Thongsornkleeb, C

Teng, L

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

[2] Fairfield Univ, Fairfield, CT 06430 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 04期

关键词：

D O I：

10.1021/ol991342g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Allytic ethers are converted to the corresponding alcohol or phenol in virtually quantitative yield at temperatures below ambient simply by stirring a hydrocarbon solution of the ether with 1 molar equiv of tert-butyllithium. The reaction, which produces 4,4-dimethyl-1-pentene as a coproduct, most likely involves an S(N)2' attack of the organolithium on the allyl ether.

引用

页码：489 / 491

页数：3

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