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South African Journal of Chemistry
versión On-line ISSN 1996-840X
versión impresa ISSN 0379-4350
S.Afr.j.chem. (Online) vol.61 Durban 2008
RESEARCH ARTICLE
NBS as a powerful catalyst for the synthesis of β-hydroxysulphides with thiolysis of epoxides under mild reaction conditions
Amin RostamiI, *; Hadi JafariII
IDepartment of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj 66177-15143, Iran
IIFaculty of Science, Islamic Azaad University of Sanandaj, Sanandaj, Iran
ABSTRACT
N-Bromosuccinimide (NBS) catalyses the ring opening of various epoxides with different thiols in CH3CN at room temperature under mild reaction conditions. The corresponding β-hydroxysulphides are obtained in short reaction times and in good to high yields with nearly complete regioselectivity. The catalyst was compared with previously reported catalysts and only one that we have found [B(C6F5)3] gave the same regioselectivity, but the reaction time was much longer (4 h versus 5 min) and the yield was considerably lower. Zn(ClO4)2.6H2O gave slightly lower selectivity but higher yields. The reaction time was about 12 times longer.
Keywords: N-Bromosuccinimide, thiols, ring opening, epoxides, β-hydroxysulphides
Full text available only in pdf format.
Acknowledgements
The authors thank the University of Kurdistan Research Councils for partial support of this work.
References
1 V. Kesavan, D. Bonnet-Delpon and J.-P. Begue, Tetrahedron Lett., 2000, 41, 2895-2898. [ Links ]
2 S. Ozaki, E. Matsui, H. Yoshinaga and S. Kitagawa, Tetrahedron Lett., 2000, 41, 2621-2624. [ Links ]
3 T. Hashiyama, Med. Res. Rev., 2000, 20, 485-501. [ Links ]
4 M.J. Martinelly, R. Vaidyanathan, VV. Khaun and M.A. Staszak, Tetrahedron Lett., 2002, 43, 3365-3367. [ Links ]
5 T. Furutani, R. Imashiro, M. Hatsuda and M. Seki, J. Org. Chem., 2002, 67, 4599-4601. [ Links ]
6 M. Chini, P. Crotti, E. Giovanni, F. Macchia and M. Pineschi, Synlett, 1992, 303-305. [ Links ]
7 D. Albanese, D. Landini and M. Penso, Synthesis, 1994, 34-36. [ Links ]
8 S. Chandrasekhar, C.R. Reddy, B.N. Babu and G. Chandrashekar, Tetrahedron Lett., 2002, 43, 3801-3803. [ Links ]
9 M.M. Mojtahedi, H. Abassi, M. Saeed Abaee and B. Mohebali, Monatsh. Chem, 2006, 137, 455-458. [ Links ]
10 V. Polshettiwar and M. P. Kaushik, Catal. Commuw., 2004, 5, 515-518. [ Links ]
11 H. Firouzabadi, N. Iranpoor, A.A. Jafari and S. Makarem, J. Mol. Catal. A: Chem., 2006, 250, 237-242. [ Links ]
12 F. Fringuelli, F. Pizzo, S. Tortoioli and L. Vaccaro, J. Org. Chem., 2003, 68, 8248-8251. [ Links ]
13 N. Azizi and M.R. Saidi, Catal. Commuw., 2006, 7, 224-227. [ Links ]
14 J.X. Chen, H.Y. Wu, C. Jin, X.X. Zhang, Y.Y. Xie and W.K. Su, Greew Chem., 2006, 8, 330-332. [ Links ]
15 B.P. Bandgar, A.V. Patil, O.S. Chavan and VT. Kamble, Catal. Commuw., 2007, 8, 1065-1069. [ Links ]
16 Shivani and A.K. Chakraborti, J. Mol. Catal. A: Chem., 2007, 263, 137-142. [ Links ]
17 C. Ogawa, N. Wang and S. Kobayashi, Chem. Lett., 2007, 36, 34-35. [ Links ]
18 F. Fringuelli, F. Pizzo, C. Vittoriani and L. Vaccaro, Eur. J. Org. Chem., 2006, 1231-1236. [ Links ]
19 M.V. Nandakumar, A. Tschop, H. Krautscheid and C. Schneider, Chem. Commuw., 2007, 2756-2758. [ Links ]
20 M.M. Mojtahedi, M.H. Ghasemi, M. Saeed Abaee and M. Bolourtchian, Arkivoc, 2005, 68-73. [ Links ]
21 M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammad-poor-Baltork and S.A. Taghavi, Catal Commuw., 2007, 8, 2087-2095. [ Links ]
22 M.M. Mojtahedi, M.S. Abaee, M. Bolourtchian and H. Abbasi, Phosphorus, Sulfur, 2007, 182, 905-910. [ Links ]
23 B.P. Bandgar, N.S. Joshi, V.T. Kamble and S.S. Sawant, Aust. J. Chem., 2008, 61, 231-234. [ Links ]
24 S.M. Abaee, M.M. Mojtahedi, H. Abbasi and E.R. Fatemi, Sywthetic Commuw, 2008, 38, 282-289. [ Links ]
25 (a) P.I. Dalko and L. Moisan, Awgew. Chem. Iwt. Ed. Ewgl., 2004, 43, 5138-5175; (b) R.O. Duthaler, Awgew. Chem. Iwt. Ed. Ewgl., 2003, 42, 975-978. [ Links ]
26 (a) A. Khazaei, A.A. Manesh and A. Rostami, J. Chem. Res - S, 2004, 695-696; (b) A. Khazaei, A. Rostami, Z. Tanbakochian and Z. Zinati, J. Braz. Chem. Soc., 2006, 17, 206-208; (c) A. Khazaei, A. Rostami and M. Mahboubifar, Catal. Commuw., 2007, 8, 383-388; (d) A. Khazaei, A. Rostami, A. Raiatzadeh and M. Mahboubifar, Caw. J. Chem., 2007, 85, 336-340; (e) A. Rostami, M. Mahboubifar and A. Khazaei, S. Afr. J. Chem., 2008, 61, 9-12. [ Links ]
27 K. Taraknath, Sywlett, 2006, 496-497. [ Links ]
28 B. Karimi, G.R. Ebrahimian and H. Seradj, Org. Lett., 1999, 1, 1737-1739. [ Links ]
29 B. Karimi, H. Seradj and G.R. Ebrahimian, Sywlett, 2000, 623-624. [ Links ]
30 B. Karimi and H. Seradj, Sywlett, 2001, 519-520. [ Links ]
Received 24 April 2008
Revised 16 September 2008
Accepted 19 September 2008
* To whom correspondence should be addressed. E-mail:a_rostami372@yahoo.com, a.rostami@uok.ac.ir