South African Journal of Chemistry
On-line version ISSN 1996-840X
ROSTAMI, Amin and JAFARI, Hadi. NBS as a powerful catalyst for the synthesis of β-hydroxysulphides with thiolysis of epoxides under mild reaction conditions. S.Afr.j.chem. (Online) [online]. 2008, vol.61, pp. 115-118. ISSN 1996-840X.
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; B-hydroxysulphides.