Highly selective cleavage of prenyl ethers by means of a TiCl4- n-Bu4NI mixed reagent

被引：26

作者：

Tsuritani, T ^{[1
]}

Shinokubo, H ^{[1
]}

Oshima, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 46期

关键词：

deprotection; ethers; titanium; titanium compounds; ammonium salts;

D O I：

10.1016/S0040-4039(99)01717-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of the prenyl ether of ethyl salicylate with a TiCl4-n-Bu4NI mixed reagent resulted in cleavage of the C-O bond to provide ethyl salicylate in quantitative yield. On the other hand, no cleavage reaction was observed when ethyl p-prenyloxybenzoate was used as a substrate. In this system, the cleavage reaction of ethers proved to be accelerated by the chelating effect of a neighboring group in the substrate. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8121 / 8124

页数：4

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