Thiirane


Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S. It is the smallest sulfur-containing heterocycle and the simplest episulfide. Like many organosulfur compounds, this species has a stench. Thiirane is also used to describe any derivative of the parent ethylene sulfide.

Structure

According to electron diffraction, the C-C and C-S distances in ethylene sulfide are respectively 1.473 and 1.811 Å. The C-C-S and C-S-C angles are respectively 66.0 and 48.0°.

Preparation and reactions

It can be prepared by the reaction of ethylene carbonate and KSCN. For this purpose the KSCN is first melted under vacuum to remove water.
Ethylenesulfide adds to amines to afford 2-mercaptoethylamines, which are good chelating ligands.
This process is often called mercaptoethylation.
Oxidation of thiirane with periodate gives ethylene episulfoxide.