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

doi:10.6023/cjoc201206012

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2162-2165.DOI: 10.6023/cjoc201206012 Previous Articles Next Articles

Notes

高立体、区域选择性合成(Z)-1-芳硫基-2-芳硒基烯

谭平^a,b, 李宁波^b, 许新华^b

a 湖南机电职业技术学院生物与化学工程系长沙 410151;
b 湖南大学化学化工学院长沙 410082

收稿日期:2012-06-10 修回日期:2012-07-13 发布日期:2012-07-19
通讯作者: 许新华 E-mail:xhx1581@yahoo.com.cn
基金资助:
国家自然科学基金(No. 21172061)资助项目.

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

Tan Ping^a,b, Li Ningbo^b, Xu Xinhua^b

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:2012-06-10 Revised:2012-07-13 Published:2012-07-19
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172061).

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]. Chin. J. Org. Chem., 2012, 32(11): 2162-2165.

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高立体、区域选择性合成(Z)-1-芳硫基-2-芳硒基烯

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

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