Insights into the reaction of trans-diarylethenes with thionyl chloride: a practical synthesis of chlorobenzo[b]thiophenes
Insights into the reaction of trans-diarylethenes with thionyl chloride: a practical synthesis of chlorobenzo[b]thiophenes
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DOI：
10.1016/j.tet.2011.09.060
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发表时间：
2011-11-18
期刊：
影响因子：
2.1
通讯作者：
Meng, Jiben
中科院分区：
文献类型：
--
作者：
Han, Jie;Wang, Qiong;Meng, Jiben
研究了各种反式-1，2-二芳基乙烯与亚硫酰氯的反应性。在温和条件下，所有底物均能以中等产率得到3-氯苯并[B]噻吩类化合物和一对苏式和邻式-1，2-二氯-1，2-二芳基乙烷类化合物。首次发现苯环上带有甲氧基的1，2-二氯-1，2-二芳基乙烷的非对映异构体在亚硫酰氯作用下也可转化为氯苯并[B]噻吩。该化学转变机理合理，并成功地应用于一锅法合成含苯并[B]噻吩和1，3，4-恶二唑单元的新型荧光液晶化合物。并对它们的光谱行为和介晶行为进行了描述。(C)2011爱思唯尔有限公司保留所有权利。
The reactivity of a variety of trans-1,2-diarylethenes with thionyl chloride has been investigated. All the substrates could readily afford 3-chlorobenzo[b]thiophenes in moderate yields and a pair of threo- and erythro-1,2-dichloro-1,2-diarylethanes as the minor products under mild condition. The diastereoisomers of 1,2-dichloro-1,2-diarylethanes with a methoxy group on the benzene ring were found for the first time to be also converted into cholobenzo[b]thiophenes under treatment of thionyl chloride. The chemical transformations have been mechanistically rationalized and successfully applied to a one-pot synthesis of novel fluorescent liquid crystalline compounds containing benzo[b]thiophene and 1,3,4-oxadiazole units. Their spectroscopic and mesogenic behaviours are also described. (C) 2011 Elsevier Ltd. All rights reserved.