KOH-Catalyzed Synthesis of O,O-Dialkyl-S-aryl Phosphoroselenoates Activated by Novel Calix[4]arene

doi:10.6023/cjoc201506018

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2636-2641.DOI: 10.6023/cjoc201506018 Previous Articles Next Articles

Notes

新型杯[4]芳烃活化KOH催化合成O,O-二烷基-S-芳(烷)基磷酸酯

欧阳跃军^a,b, 邱仁华^b, 陈四海^b, 陈锦杨^b, 许新华^b

a 怀化学院化学与化学工程系怀化 428000;
b 湖南大学化学化工学院长沙 410082

收稿日期:2015-06-15 修回日期:2015-08-05 发布日期:2015-08-26
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)、湖南省科技计划(No. 2013FJ3023)资助项目.

KOH-Catalyzed Synthesis of O,O-Dialkyl-S-aryl Phosphoroselenoates Activated by Novel Calix[4]arene

Ouyang Yuejun^a,b, Qiu Renhua^b, Chen Sihai^b, Chen Jinyang^b, Xu Xinxu^b

a Department of Chemistry and Chemical Engineering, Huaihua University, Huaihua 418000;
b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2015-06-15 Revised:2015-08-05 Published:2015-08-26
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21273068, 21172061), the Planned Science and Technology Project of Hunan Province (No. 2013FJ3023).

1. KOH-Catalyzed Synthesis of O,O-Dialkyl-S-aryl Phosphoroselenoates Activated by Novel Calix[4]arene.PDF(2878KB)

Abstract

A novel calix[4]arene 3 was synthesized. The experimental results show that the reactions of O,O-dialkylphos- phonates and diaryl(alkyl) disulfides proceed efficiently in the presence of calix[4]arene 3 (5.0 mol%) and KOH (20 mol%), affording O,O-dialkyl-S-aryl(alkyl)phosphoroselenoates in good to excellent yields. The yields of desired products do not reduce after recycling for 6 times of calix[4]arene 3. Hence, a convenient and efficient method for the preparation of O,O-dial- kyl-S-aryl(alkyl)phosphoroselenoates was provided, avoiding the use of some foul and toxic reagents.

Key words: novel calix[4]arene, diaryl(alkyl) disulfide, O,O-dialkylphosphonate, O,O-dialkyl-S-aryl(alkyl)phosphoro-selenoate

Cite this article

Ouyang Yuejun, Qiu Renhua, Chen Sihai, Chen Jinyang, Xu Xinxu. KOH-Catalyzed Synthesis of O,O-Dialkyl-S-aryl Phosphoroselenoates Activated by Novel Calix[4]arene[J]. Chin. J. Org. Chem., 2015, 35(12): 2636-2641.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Iwamoto, K.; Araki, K.; Shinkai, S. Tetrahedron 1991, 47, 4325.
[2] Verboom, W.; Datta, S.; Asfari, Z. J. Org. Chem. 1992, 57, 5394.
[3] Taniguchi, H.; OtsuJi, Y.; Nomura, E. Bull. Chem. Soc. Jpn. 1995, 68, 3563.
[4] Perrin, R.; Lamartine, R.; Perrin, M. Pure Appl. Chem. 1993, 65, 1549.
[5] Taniguchi, H.; Nomura, E. Chem. Lett. 1988, 10, 1773.
[6] Nomura, E.; Taniguchi, H.; Kawaguchi, K. J. Org. Chem. 1993, 58, 4709.
[7] Shimizu, S.; Kito, K.; Sasaki, Y. Chem. Commun. 1997, 1629.
[8] Shinkai, S.; Mori, S.; Koreishi, H. J. Am. Chem. Soc. 1986, 108, 2409.
[9] Cacciapaglia, R.; Casnati, A.; Mandolini, L. Chem. Commun. 1992, 1291.
[10] Cacciapaglia, R.; Casnati, A.; Mandolini, L. J. Am. Chem. Soc. 1992, 114, 10956.
[11] Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303.
[12] Almgren, M.; Grieser, F.; Thomas, J. K. J. Am. Chem. Soc. 1979, 101, 279.
[13] Fendler, J. H.; Fendler, E. J.; Infante, G. A. J. Am. Chem. Soc. 1975, 97, 89.
[14] Zio?kowski, M.; Grabowski, S. J.; Leszczynski, J. J. Chem. Phy. 2009, 355, 169.
[15] Pendas, A. M.; Blanco, M. A.; Francisco, E. J. Phys. Chem. 2006, 125, 184112.
[16] Hay, B. P.; Firman, T. K.; Moyer, B. A. J. Am. Chem. Soc. 2005, 127, 1810.
[17] Fukuoka, M.; Shuto, S.; Minakawa, N. Tetrahedron Lett. 1999, 40, 5361.
[18] Fukuoka, M.; Shuto, S.; Minakawa, N. J. Org. Chem. 2000, 65, 5238.
[19] Huang, L. J.; Zhao, Y. Y.; Yuan, L. J. Med. Chem. 2002, 45, 5340.
[20] Lopin, C.; Gouhier, G.; Gautier, A. J. Org. Chem. 2003, 68, 9916.
[21] Liu, D. D.; Chen, D. W.; Chen, Z. C. Synth. Commun. 1992, 22, 2903.
[22] Watanabe, Y.; Inoue, S.; Yamamoto, T. Synthesis 1995, 1243.
[23] Ye, J. D.; Barth, C. D.; AnJaneyulu, P. S. R. Org. Biomol. Chem. 2007, 5, 2491.
[24] Gao, Y. X.; Tang, G.; Zhao, Y. F. Synthesis 2009, 1081.
[25] Li, Y. Y.; Chen, S. H.; Su, L.; Li, J. H.; Xu, X. H. Chin. J. Org. Chem. 2013, 33, 1999 (in Chinese). (李媛媛, 陈四海, 苏柳, 李建华, 许新华, 有机化学, 2013, 33, 1999.)
[26] Percec, V.; Bera, T. K.; De, B. B. J. Org. Chem. 2001, 66, 2104.
[27] Dong, W. L.; Huang, G. Y.; Li, Z. M.; Zhao, W. G. Phosphorus, Sulfur, Silicon Relat. Elem. 2009, 184, 2058.
[28] He, Y.; Huang, D.; Lu, M. Phosphorus, Sulfur, Silicon Relat. Elem. 2012, 187, 1118.
[29] Ouyang, Y. J.; Li, Y. Y.; Li, N. B.; Xu, X. H. Chin. Chem. Lett. 2013, 24, 1103.
[30] Xu, Q.; Liang, C. G.; Hunag, X. Synth. Commun. 2003, 33, 2777.
[31] Torii, S.; Tanaka, H.; Sayo, N. J. Org. Chem. 1979, 44, 2938.

新型杯[4]芳烃活化KOH催化合成O,O-二烷基-S-芳(烷)基磷酸酯

KOH-Catalyzed Synthesis of O,O-Dialkyl-S-aryl Phosphoroselenoates Activated by Novel Calix[4]arene

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 0

Recommended Articles

Metrics

Comments