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

doi:10.6023/cjoc201304024

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (9): 1999-2003.DOI: 10.6023/cjoc201304024 Previous Articles Next Articles

Notes

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

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 发布日期:2013-05-13
通讯作者: 许新华 E-mail:xhx1581@hnu.edu.cn
基金资助:
国家自然科学基金(Nos. 21273068, 21172061, J1210040, J1103312)资助项目

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

Li Yuanyuan, Chen Sihai, Su Liu, Li Jianhua, Xu Xinhua

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2013-04-17 Revised:2013-04-28 Published:2013-05-13
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21273068, 21172061, J1210040, J1103312)

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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Li Yuanyuan, Chen Sihai, Su Liu, Li Jianhua, Xu Xinhua. Synthesis of O,O-Dialkyl-Se-aryl Phosphoroselenoates Catalyzed by Cesium Hydroxide[J]. Chin. J. Org. Chem., 2013, 33(9): 1999-2003.

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氢氧化铯催化O,O-二烷基-Se-芳基磷酸酯的合成

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

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