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South African Journal of Chemistry

On-line version ISSN 1996-840X
Print version 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.

 

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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

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