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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 11: 2162 - 2165

DOI: https://doi.org/10.6023/cjoc201206012

Notes

Highly Regio- and Stereo-selective Synthesis of (Z)-1-Arylthio-2-Arylseleno Alkenes

  • Tan Ping ,
  • Li Ningbo ,
  • Xu Xinhua
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  • a Department of Biological and Chemical Engineering, Hunan Mechanical and Electrical Polytechnic, Changsha 410151;
    b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received date: 2012-06-10

  Revised date: 2012-07-13

  Online published: 2012-07-19

Supported by

Project supported by the National Natural Science Foundation of China (No. 21172061).

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Abstract

In the presence of catalytic amount of cesium hydroxide, the nucleophilic addition reaction of selenols to alkyne sulfurnides occurred in tetrahydrofuran at room temperature under nitrogen atmosphere to give highly regio- and stereo-selective (Z)-1-arylthio-2-arylseleno alkenes in 70%～93% yields. The mechanism involved the formation of cesium arylselenides and the nucleophilic addition to the alkynyl sulfides in the presence of cesium hydroxide. The corresponding alkenes were obtained upon hydrolysis.

Key words： nucleophilic addition; regioselectivity; alkynyl thioether; cesium hydroxide; (Z)-1-arylthio-2-arylseleno alkenes

Cite this article

Tan Ping , Li Ningbo , Xu Xinhua . Highly Regio- and Stereo-selective Synthesis of (Z)-1-Arylthio-2-Arylseleno Alkenes[J]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2162 -2165 . DOI: 10.6023/cjoc201206012

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