ORTHO-LITHIATION VIA A CARBONYL SYNTHON

被引：50

作者：

HARRIS, TD

ROTH, GP

机构：

[1] Department of Chemistry, SUNY-Fredonia, New York 14063, Fredonia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 12期

关键词：

D O I：

10.1021/jo01326a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of the imidazolidine ring as an ortho-directing group in aryl and aralkyl metalation is described. This carbonyl synthon directs lithiation to the ortho position nearly quantitatively and affords the corresponding aromatic aldehyde on mild acid hydrolysis. Thus, lithiation of 1,3-dimethyl-2-phenylimidazolidine (1) with n-butyllithium-TMEDA, quenching with methyl iodide, and hydrolysis with 2 N HCl gave o-tolualdehyde (3) in 95% yield. The generality of this technique is discussed. © 1979, American Chemical Society. All rights reserved.

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页码：2004 / 2007

页数：4

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