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含分子内氢键的苯硫酚在水相中的Michael加成反应
引用本文:高照波,邱雪鹏,郭海泉,康传清,高连勋. 含分子内氢键的苯硫酚在水相中的Michael加成反应[J]. 高等学校化学学报, 2004, 25(8): 1471-1473
作者姓名:高照波  邱雪鹏  郭海泉  康传清  高连勋
作者单位:中国科学院长春应用化学研究所, 高分子物理与化学国家重点实验室, 长春130022
摘    要:苯硫酚的巯基是一个较强的亲核基团,对α,β-不饱和双键的Michael加成反应已有报道.但是当巯基的邻位存在与其形成氢键的基团时,如果按文献条件进行反应,或者反应无法进行,或者要使用反应条件苛刻的丁基锂,或者使用吡啶等毒性较大的反应溶剂,而且产率较低.本文选择

关 键 词:水相反应  苯硫酚  分子内氢键  Michael加成  
文章编号:0251-0790(2004)08-1471-03
收稿时间:2003-06-30

Michael Addition Reaction of Thiophenol with Intramolecular Hydrogen Bond in Aqueous Medium
GAO Zhao-Bo,QIU Xue-Peng,GUO Hai-Quan,KANG Chuan-Qing,GAO Lian-Xun. Michael Addition Reaction of Thiophenol with Intramolecular Hydrogen Bond in Aqueous Medium[J]. Chemical Research In Chinese Universities, 2004, 25(8): 1471-1473
Authors:GAO Zhao-Bo  QIU Xue-Peng  GUO Hai-Quan  KANG Chuan-Qing  GAO Lian-Xun
Affiliation:State Key Lab of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
Abstract:The method of Michael addition reaction of thiophenol with intramolecular hydrogen bond in an aqueous medium was reported. The aqueous reactive medium includes saturated sodium bicarbonate solution and catalytic amount of tetrabutylammonium bisulfate. 2-Hydroxythiophenol,2-aminothiophenol,2-carboxythiophenol,ethyl acrylate and arcylonitrile were selected as model molecules to demonstrate the method. It is found that the reaction can be accomplished rapidly at room temperature with a high yield,and no mercapto-coupling byproduct formed.
Keywords:Aqueous reaction  Thiophenol  Intramolecular hydrogen bond  Michael addition
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