The first example of 2,2-dilithiocyanocyclopropanes:: generation from 2-bromo-2-sulfinylcyanocyclopropanes with tert-butyllithium, property, and a synthesis of fully substituted cyanocyclopropanes

被引：4

作者：

Fukushima, Iori ^{[1
]}

Gouda, Youhei ^{[1
]}

Satoh, Tsuyoshi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Dept Chem, Fac Sci, Shinjuku Ku, Tokyo 1620826, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 10期

关键词：

geminal dianion; 1,1-dilithiocyclopropane; cyanocyclopropane; sulfoxide-lithium exchange; bromine-lithium exchange;

D O I：

10.1016/j.tetlet.2006.12.148

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,2-Dilithiocyanocyclopropanes were easily generated from 2-bromo-2-(p-tolylsulfinyl)cyanocyclopropanes with tertbutyllithium in toluene at -78 degrees C through concomitant sulfoxide-lithium and bromine-lithium exchange reactions. The gem-di-anions were found to be stable at -78 degrees C for at least 30 min. Reaction of the gem-dianions with electrophiles gave fully substituted cyanocyclopropanes in moderate yields. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1855 / 1858

页数：4

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