An Unusual Synthesis of Tröger’s Bases Using DMSO/HCl as Formaldehyde Equivalent

Zhong Li; Xiaoyong Xu; Yanqing Peng; Zhaoxing Jiang; Chuanyong Ding; Xuhong Qian

doi:10.1055/s-2005-861868

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Synthesis 2005(8): 1228-1230
DOI: 10.1055/s-2005-861868

SHORTPAPER

An Unusual Synthesis of Tröger’s Bases Using DMSO/HCl as Formaldehyde Equivalent

Zhong Li*^a,b, Xiaoyong Xu^a, Yanqing Peng^a, Zhaoxing Jiang^a, Chuanyong Ding^a, Xuhong Qian*^b
^a Shanghai Key Lab of Chemistry Biology, Institute of Pesticides and Pharmaceuticals, East China University of Science and Technology, P.O. Box 544,130, Meilong Road Shanghai 200237, P. R. China
^b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, P. R. China
Fax: +86(21)64252603; e-Mail: lizhong@ecust.edu.cn;

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Publication History

Received 3 December 2004
Publication Date:
10 March 2005 (online)

Abstract
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Abstract

The reactions between anilines and DMSO/HCl produce Tröger’s bases in moderate yield. The Tröger’s bases bearing an electron-withdrawing group can also be synthesized through this procedure. In this reaction, DMSO/HCl acts as formaldehyde equivalent.

Key words

Tröger’s bases - DMSO/HCl - formaldehyde equivalent

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