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Chinese Journal of Organic Chemistry >

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

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

Notes

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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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

Cite this article

Li Yuanyuan , Chen Sihai , Su Liu , Li Jianhua , Xu Xinhua . Synthesis of O,O-Dialkyl-Se-aryl Phosphoroselenoates Catalyzed by Cesium Hydroxide[J]. Chinese Journal of Organic Chemistry, 2013 , 33(9) : 1999 -2003 . DOI: 10.6023/cjoc201304024

References

[1] Ogawa, A.; Tanaka, H.; Yokoyama, H.; Obayashi, R.; Yokoyama, K.; Sonada, N. J. Org. Chem. 1992, 57, 111.
[2] Chuang, C.-P.; Wang, S.-F. Synth. Commun. 1995, 25, 3459.
[3] Chen, D.-J.; Chen, Z.-C. Synth. Commun. 2001, 31, 421.
[4] Marinozzi, M.; Fulco, M. C.; Rizzo, R.; Pellicciari, R. Synlett 2004, 1027.
[5] Gautier, A.; Garipova, G.; Dubert, O.; Oulyadi, H.; Piettre, S. R. Tetrahedron Lett. 2001, 42, 5673.
[6] Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195.
[7] Huang, X.; Xu, Q.; Liang, C.-G.; He, Q.-W. Synth. Commun. 2002, 32, 1243.
[8] Herpin, T. F.; Houlton, J. S.; Motherwell, W. B.; Roberts, B. P.; Weibel, J. M. Chem. Commun. 1996, 613.
[9] Herpin, T. F.; Motherwell, W. B.; Roberts, B. P.; Roland, S.; Weibel, J. M. Tetrahedron 1997, 53, 15085.
[10] Lopin, C.; Gouhier, G.; Gautier, A.; Piettre, S. R. J. Org. Chem. 2003, 68, 9916.
[11] Glass, R. S.; Singh, W. P.; Jung, W.; Veres, Z.; T. D.; Stadtman, T. Biochemistry 1993, 32(47), 12556.
[12] Han, L.-B.; Choi, N.; Tanaka, M. J. Am. Chem. Soc. 1996, 118(29), 7000.
[13] Herpin, T. F. M.S. Thesis, University of London, London, 1995.
[14] Xu, Q.; Liang, C.-G.; Huang, X. Synth. Commun. 2003, 33, 2777.
[15] Chen, J.-M.; Huang, X. Synth. Commun. 2004, 34, 1745.
[16] Chen, D.-J.; Chen, Z.-C. J. Chem. Res., Synop. 2000, 370.
[17] Gao, Y.-X.; Tang, G.; Zhao, Y.-F. Synthesis 2009, 1081.
[18] Zhang, Q.-L.; Zeng, J.-C.; Xu, X.-H.; Zhou, B.; Lu, R.-L.; Chen, X.; Li, Y.-J. Chem. J. Chin. Univ. 2005, 26, 2046 (in Chinese).
(张秋林, 曾纪朝, 许新华, 周冰, 卢锐亮, 陈雄, 李言杰, 高等学校化学学报, 2005, 26, 2046.)
[19] Xia, X.; Zou, K.-B.; Li, R.-X.; Zhang, Z.-Y.; Shao, L.-L.; Fang, D.-W.; Xu, X.-H. Acta Chim. Sin. 2008, 66, 1749 (in Chinese).
(夏湘, 邹康兵, 李若信, 张尊英, 邵玲玲, 方大为, 许新华, 化学学报, 2008, 66, 1749.)
[20] Xia, X.; Li, J.-P.; Zou, K.-B.; Fang, D.-W.; Zhang, Z.-Y.; Xu, Y.-L.; Xu, X.-H. Chin. J. Org. Chem. 2009, 29, 112 (in Chinese).
(夏湘, 李剑平, 邹康兵, 方大为, 张尊英, 徐艳丽, 许新华, 有机化学, 2009, 29, 112.)
[21] Wang, X.-Y.; Li, Z.-Z.; Zhang, W.-J.; Wang, X.; Chen, J.-Y.; Li, N.-B.; Qiu, R.-H.; Xu, X.-H. Chin. J. Org. Chem. 2013, 33, 558 (in Chinese).
(王小勇, 李治章, 张卫军, 王勰, 陈锦杨, 李宁波, 邱仁华, 许新华, 有机化学, 2013, 33, 558.)
[22] Karimi, B.; Hazarkhani, H.; Zareyee, D. Synthesis 2002, 2513.
[23] Wallace, T. J.; Schriesheim, A.; Bartok, W. J. Org. Chem. 1963, 28, 1311.
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