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2013 , Vol. 33 >Issue 9: 1999 - 2003

DOI: https://doi.org/10.6023/cjoc201304024

研究简报

氢氧化铯催化O,O-二烷基-Se-芳基磷酸酯的合成

  • 李媛媛 ,
  • 陈四海 ,
  • 苏柳 ,
  • 李建华 ,
  • 许新华
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  • 湖南大学化学化工学院 长沙 410082

收稿日期: 2013-04-17

  修回日期: 2013-04-28

  网络出版日期: 2013-05-13

基金资助

国家自然科学基金(Nos. 21273068, 21172061, J1210040, J1103312)资助项目

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Synthesis of O,O-Dialkyl-Se-aryl Phosphoroselenoates Catalyzed by Cesium Hydroxide

  • Li Yuanyuan ,
  • Chen Sihai ,
  • Su Liu ,
  • Li Jianhua ,
  • Xu Xinhua
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  • College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received date: 2013-04-17

  Revised date: 2013-04-28

  Online published: 2013-05-13

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21273068, 21172061, J1210040, J1103312)

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摘要

在催化量氢氧化铯存在下, O,O-二烷基膦酸酯与二芳基二硒醚在DMSO中、室温、空气氛中反应, 高收率得到磷酸硒酯. 反应机理为氢氧化铯与O,O-二烷基膦酸酯反应生成的(RO)2P-(O)Cs+, (RO)2P-(O)Cs+亲核进攻ArSeSeAr生成磷酸硒酯和ArSe-Cs+, 后者在水存在下, 被氧化得到ArSeSeAr和氢氧化铯. 这方法为合成磷酸硒酯提供了一条简便有效的路径.

关键词： 氢氧化铯; 二芳基二硒醚; O,O-二烷基-Se-苯基膦酸酯

本文引用格式

李媛媛 , 陈四海 , 苏柳 , 李建华 , 许新华 . 氢氧化铯催化O,O-二烷基-Se-芳基磷酸酯的合成[J]. 有机化学, 2013 , 33(9) : 1999 -2003 . DOI: 10.6023/cjoc201304024

Abstract

In the presence of cesium hydroxide, using dimethyl sulfoxide (DMSO) as solvent, dialkyl phosphites reacted with diaryldiselenides at room temperature to afford the corresponding Se-aryl phosphoroselenoates in high yields. The reaction mechanism is that dialkyl phosphites reacted with cesium hydroxide to give (RO)2P-(O)Cs+, which underwent nucleophilic attack on ArSeSeAr to give product Se-aryl phosphoroselenoates and ArSe-Cs+, the latter was oxidized in the presence of water to form diaryldiselenides and catalyst cesium hydroxide. The method could provide a new and expedient way for the Se-aryl phosphoroselenoates.

Key words： cesium hydroxide; diaryl diselenide; O,O-dialkyl-Se-arylphosphoroselenoates

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