10.1007/s11178-008-1003-1

Abstract

The reaction mechanism of 1,3-dihalopropan-2-ones with hydrogen sulfide in the presence of hydrogen chloride was studied in terms of the density functional theory. Unlike 1-halopropan-2-ones which give rise to 1-halo-2-sulfanylpropan-2-ols via preliminary enolization, 1,3-dihalopropan-2-ones preferentially undergo direct nucleophilic attack on the carbonyl group by hydrogen sulfide. The potential energy surface for rotational isomerism of 1,3-dihalopropane-2-thiones and 1,3-dihalo-2-sulfanylpropan-2-ols was analyzed, and their most stable rotamers were identified.