DIRECTED LITHIATION OF CHLOROBENZENES - REGIOSELECTIVITY AND APPLICATION TO A SHORT SYNTHESIS OF BENZOCYCLOBUTENES

被引：62
作者：
IWAO, M
机构：
[1] Department of Chemistry, Faculty of Liberal Arts, Nagasaki University, Nagasaki 852
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 11期
关键词：
D O I：
10.1021/jo00298a045
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chlorobenzene and its OMe, OSiMe2-£-Bu, and Cl derivatives 1 were lithiated with high regioselectivity ortho to chlorine by treatment with sec-BuLi in THF at -105 °C without complications due to benzyne formation. The lithio species thus generated underwent smooth Michael addition on treatment with l-(phenylsulfonyl)-l-(trimethylsilyl)ethene (2). The desilylated Michael adducts 3 or 6 were converted in good yields to l-(phe-nylsulfonyl)benzocyclobutenes 7 via benzyne intermediates. © 1990, American Chemical Society. All rights reserved.
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页码：3622 / 3627
页数：6
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