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http://dx.doi.org/10.5012/bkcs.2009.30.8.1832

The Rapid and Efficient Synthesis of Bromohydrins from Olefins under HBr/H2O2 System by Visible Light Induced  

Tang, Rui-Ren (School of Chemistry and Chemical Engineering, Central South University)
Gong, Nian-Hua (School of Chemistry and Chemical Engineering, Central South University)
Publication Information
Abstract
A simple and safe method has been presented for conversion of olefins into bromohydrins using hydrogen bromide and hydrogen peroxide as bromide source by visible light induced within a very short time to get high yield bromohydrins along with a little mount dibromo-product. In this paper, cyclohexene is firstly carried out as the model substrate and investigated the bromination under HBr/$H_2O_2$ system using 150 W incandescent light irradiated in C$Cl_4$ within short time to get good yield of 2-bromocyclohexanol along with a little mount of 1,2-dibromocyclohexane; then, a series of alkenes are brominated to corresponding bromohydrins using the same protocol.
Keywords
Alkenes; Bromohydrin; Dibromination; Hydrogen bromide; Hydrogen peroxide;
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1 Sels, B. F.; De Vos, D. E. ; Jacobs, P. A. J. Am. Chem. Soc. 2001, 123, 8350   DOI   ScienceOn
2 Sels, B.; Levecque, P.; Brosius, R.; De Vos, D.; Jacobs, P.; Gammon, D. W. Adv. Synth. Catal. 2005, 347, 93   DOI   ScienceOn
3 Moriuchi, T.; Yamaguchi, M.; Kikushima, K.; Hirao, T. Tetrahedron Lett. 2007, 48, 2667   DOI   ScienceOn
4 Narender, M.; Somi Reddy, M.; Nageswar, Y. V. D.; Rama Rao, K. J. Mol. Catal. A: Chem. 2006, 258, 10   DOI   ScienceOn
5 Hajra, S.; Bhowmick, M.; Karmakar, A. Tetrahedron Lett. 2005, 46, 3073   DOI   ScienceOn
6 Yadav, J. S.; Reddy, B. V. S.; Baishya, G.; Harshavardhan, S. J.; Janardhana Chary, C.; Gupta, M. K. Tetrahedron Lett. 2005, 46, 3569   DOI   ScienceOn
7 Urankar, D.; Rutar, I.; Modec, B.; Dolenc, D. Eur. J. Org. Chem. 2005, 11, 2349
8 Dieter, R. K.; Nice, S. E.; Velu, S. E. Tetrahedron Lett. 1996, 37, 2377   DOI   ScienceOn
9 Anand, N.; Kapoor, M.; Koul, S.; Taneja, S. C.; Sharma, R. L.; Qazi, G. N. Tetrahedron: Asymmetry 2004, 15, 3131   DOI   ScienceOn
10 George, S.; Narina, S. V.; Sudalai, A. Tetrahedron Lett. 2007, 48, 1375   DOI   ScienceOn
11 Clark, J. Green Chem. 1999, 1, 1   DOI   ScienceOn
12 Mestres, R.; palenzuela, J. Green Chem. 2002, 4, 314   DOI   ScienceOn
13 Mallick, S.; Parida, K. M. Catalysis Commun. 2007, 8, 889   DOI   ScienceOn
14 Barhate, N. B.; Gajare, A. S.; Wakharkar, R.; Badekar, A. V. Tetrahedron Lett. 1998, 39, 6349   DOI   ScienceOn
15 Das, B.; Venkateswarlu, K.; Damodar, K.; Suneel, K. J. Mol. Catal. A: Chem. 2007, 269, 17   DOI   ScienceOn
16 Tenaglia, A.; Pardigon, O.; Buono, G. J. Org. Chem. 1996, 61, 1129   DOI   ScienceOn
17 Cabanal-Duvillard, I.; Berrier, J. F.; Royer, J.; Husson, H. P. Tetrahedron Lett. 1998, 39, 5181   DOI   ScienceOn
18 Ranu B. C.; Banerjee, S. J. Org. Chem. 2005, 70, 4517   DOI   ScienceOn
19 Nandanan, E.; Phukan, P.; Sudalai, A. Indian J. Chem. 1999, 38B, 283
20 Hajra, S.; Karmakar, A.; Maji, T.; Medda, A. M. Tetrahedron 2006, 62, 8959   DOI   ScienceOn
21 Raghavan, S.; Abdul Rasheed, M.; Joseph, S. C.; Rajender, A. Chem. Commun. 1999, 999, 1845