Notes

Access to Cyclohexane-1,2-diol through the Diphenyldiselenide Catalyzed Oxidation of Cyclohexene by Hydrogen Peroxide

  • Yu Lei ,
  • Wang Jun ,
  • Chen Tian ,
  • Ding Kehong ,
  • Pan Yi
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  • a School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093;
    b School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002;
    c Jiangsu Yangnong Chemical Engineering Co. Ltd., Yangzhou 225009

Received date: 2012-12-30

  Revised date: 2013-01-16

  Online published: 2013-01-25

Supported by

Project supported by the National Natural Science Fundation of China (No. 21202141), the Priority Academic Program Development of Jiangsu Higher Education Institutions, the Opening Foundation of the Key Laboratory of Environmental Materials and Engineering of Jiangsu Province (Nos. K11024, K090030).

Abstract

The diphenyldiselenide catalyzed oxidation of cyclohexene by hydrogen peroxide led to cyclohexane-1,2-diol with high conversion and selectivity. Compared with traditional metal catalyst, selenium catalysts are cheaper and less harmful to environment. This synthetic method is also clean and highly atom-economic. Therefore, this reaction is highly applicable.

Cite this article

Yu Lei , Wang Jun , Chen Tian , Ding Kehong , Pan Yi . Access to Cyclohexane-1,2-diol through the Diphenyldiselenide Catalyzed Oxidation of Cyclohexene by Hydrogen Peroxide[J]. Chinese Journal of Organic Chemistry, 2013 , 33(05) : 1096 -1099 . DOI: 10.6023/cjoc2012012049

References

[1] Wang, X.-G.; Yang, Y.-Y. Chem. Interm. 2009, 5 (in Chinese).
(王小光, 杨月云, 化工中间体, 2009, 5.)
[2] Lee, D. G; Oxidation in Organic Chemistry, Academic Press, New York, 1982, Part D.
[3] Zhu, W.-M.; Ford, W. T. J. Org. Chem. 1991, 56, 7022.
[4] Wei, S.-H.; Liu, S.-T. Cat. Lett. 2009, 127, 143.
[5] (a) Metin, Ö.; Alcan Alp, N.; Akbayrak, S.; Biçer, A.; Gültekin, M. S.; Özkar, S.; Bozkaya, U. Green Chem. 2012, 14, 1488.
(b) Reddy, S. M.; Srinivasulu, M.; Reddy, Y. V.; Narasimhulu, M.; Venkateswarlu, Y. Tetrahedron Lett. 2006, 47, 5285.
[6] Kamata, K.; Hirano, T.; Kuzuya, S.; Mizuno, N. J. Am. Chem. Soc. 2009, 131, 6997.
[7] Peng, Z.-Q.; Huang, J.-F. A Summary of the Investigations on the Selenium Resources of the Word Selenium Capital Enshi, Qinghua Press, Beijing, 2012, Ver. 1, p. 42 (in Chinese).
(彭祚全, 黄剑锋, 世界硒都恩施硒资源研究概述, 清华大学出版社, 北京, 2012, 第1版, p. 42.)
[8] (a) Niyomura, O.; Cox, M.; Wirth, T. Synlett 2006, 251.
(b) Browne, D. M.; Niyomura, O.; Wirth, T. Org. Lett. 2007, 9, 3169.
(c) Drake, M. D.; Bateman, M. A.; Detty, M. R. Organometallics 2003, 22, 4158.
(d) Goodman, M. A.; Detty, M. R. Organometallics 2004, 23, 3016.
(e) Bennett, S. M.; Tang, Y.; McMaster, D.; Bright, F. V.; Detty, M. R. J. Org. Chem. 2008, 73, 6849.
(f) Zhao, D.; Johansson, M.; B?ckvall, J.-E. Eur. J. Org. Chem. 2007, 4431.
(g) Gebhardt, C.; Priewisch, B.; Irran, E.; Rück-Braun, K. Synthesis 2008, 1889.
(h) ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. J. Org. Chem. 2001, 66, 2429.
(i) Ichikawa, H.; Usami, Y.; Arimoto, M. Tetrahedron Lett. 2005, 46, 8665.
(j) Kamata, K.; Hirano, T.; Kuzuya, S.; Mizuno, N. J. Am. Chem. Soc. 2009, 131, 6997.
(k) Santoro, S.; Santi, C.; Sabatini, M.; Testaferri, L.; Tiecco, M. Adv. Synth. Catal. 2008, 350, 2881.
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