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Insights into the reaction of trans-diarylethenes with thionyl chloride: a practical synthesis of chlorobenzo[ b]thiophenes

The reactivity of a variety of -1,2-diarylethenes with thionyl chloride has been investigated. All the substrates could readily afford 3-chlorobenzo[ ]thiophenes in moderate yields and a pair of - and -1,2-dichloro-1,2-diarylethanes as the minor products under mild condition. The diastereoisomers of... Full description

Journal Title: Tetrahedron 2011, Vol.67(46), pp.8865-8872
Main Author: Han, Jie
Other Authors: Wang, Qiong , Chang, Xiaoyong , Liu, Yuxin , Wang, Yanmei , Meng, Jiben
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0040-4020 ; E-ISSN: 1464-5416 ; DOI: 10.1016/j.tet.2011.09.060
Link: https://www.sciencedirect.com/science/article/pii/S0040402011014177
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recordid: elsevier_sdoi_10_1016_j_tet_2011_09_060
title: Insights into the reaction of trans-diarylethenes with thionyl chloride: a practical synthesis of chlorobenzo[ b]thiophenes
format: Article
creator:
  • Han, Jie
  • Wang, Qiong
  • Chang, Xiaoyong
  • Liu, Yuxin
  • Wang, Yanmei
  • Meng, Jiben
subjects:
  • Benzo[ B]Thiophene
  • Trans-Diarylethene
  • Thionyl Chloride
  • Oxadiazole
  • Liquid Crystals
  • Chemistry
ispartof: Tetrahedron, 2011, Vol.67(46), pp.8865-8872
description: The reactivity of a variety of -1,2-diarylethenes with thionyl chloride has been investigated. All the substrates could readily afford 3-chlorobenzo[ ]thiophenes in moderate yields and a pair of - and -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[ ]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[ ]thiophene and 1,3,4-oxadiazole units. Their spectroscopic and mesogenic behaviours are also described.
language: eng
source:
identifier: ISSN: 0040-4020 ; E-ISSN: 1464-5416 ; DOI: 10.1016/j.tet.2011.09.060
fulltext: fulltext
issn:
  • 0040-4020
  • 00404020
  • 1464-5416
  • 14645416
url: Link


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titleInsights into the reaction of trans-diarylethenes with thionyl chloride: a practical synthesis of chlorobenzo[ b]thiophenes
creatorHan, Jie ; Wang, Qiong ; Chang, Xiaoyong ; Liu, Yuxin ; Wang, Yanmei ; Meng, Jiben
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subjectBenzo[ B]Thiophene ; Trans-Diarylethene ; Thionyl Chloride ; Oxadiazole ; Liquid Crystals ; Chemistry
descriptionThe reactivity of a variety of -1,2-diarylethenes with thionyl chloride has been investigated. All the substrates could readily afford 3-chlorobenzo[ ]thiophenes in moderate yields and a pair of - and -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[ ]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[ ]thiophene and 1,3,4-oxadiazole units. Their spectroscopic and mesogenic behaviours are also described.
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