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 highly unpleasant odour. Thiirane is also used to describe any derivative of the parent ethylene sulfide.
Structure and properties
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°. The microwave and infrared spectra were studied experimentally and computationally.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.