Thiirane
Template:Chembox Script error: No such module "For". Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S.[1] 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°.[2] The microwave and infrared spectra were studied experimentally and computationally.[3]
Preparation and reactions
It can be prepared by the reaction of ethylene carbonate and KSCN.[4] For this purpose the KSCN is first melted under vacuum to remove water.
- KSCN + C2H4O2CO → KOCN + C2H4S + CO2
Ethylenesulfide adds to amines to afford 2-mercaptoethylamines,[5] which are good chelating ligands.
- C2H4S + R2NH → R2NCH2CH2SH
This process is often called mercaptoethylation.[6]
Oxidation of thiirane with periodate gives ethylene episulfoxide.
References
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- ↑ R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). Template:ISBN.
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