Reaction of alkene oxides oxiranes with sulfur compounds

Reaction of alkene oxides (oxiranes) with sulfur compounds 

Alkene oxides (oxiranes) can be converted into the corresponding sulfides (thiiranes) with replacement of the oxygen by sulfur under the action of sulfur-containing compounds such as, e.g., thiocyanates, sodium thiosulfate, or thiourea 377-381 

The reaction is often very violent and good cooling is required. 

The preparation of cyclohexene sulfide (7-thiobicyclo [4.1.0 Jheptane)378 3 82 may be described as an example Cyclohexene oxide (7-oxabicyclo[4.1.0]heptane) (5 g) in methanol (20 ml) is treated with thiourea (5 g) at 60° for 1.5 h. The mixture is poured into water (150ml) and extracted with chloroform. Fractionation affords the sulfide, b.p. 67-68716 mm, in 58% yield. 

Oxiranes can also be cleaved by mercaptanes, this yielding -hydroxy sulfides. This reaction has been carried out386 with oxirane, 7-oxabicyclo[4.2.1]heptane, and epichlorohydrin [(chloromethyl)oxirane] and, as sulfur components, ethane-, 1-propane-, benzene-, and a toluene-thiol in the presence of a little active charcoal as catalyst. 

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