Thiete

Thiete is a heterocyclic compound containing an unsaturated four-membered ring with three carbon atoms and one sulfur atom.^[1][2][3] It is more commonly encountered not on its own, but in anellated derivatives, several of which have been synthesized. Thietes are generally not very stable.^[4]

Thiete

Names
Preferred IUPAC name 2H-Thiete
Other names 1-Thiacyclobut-2-ene
Identifiers
CAS Number	503-31-1
3D model (JSmol)	Interactive image
ChemSpider	2659702 N
PubChem CID	3415867
CompTox Dashboard (EPA)	DTXSID30392288
InChI InChI=1S/C3H4S/c1-2-4-3-1/h1-2H,3H2 N Key: HPINPCFOKNNWNW-UHFFFAOYSA-N N InChI=1/C3H4S/c1-2-4-3-1/h1-2H,3H2 Key: HPINPCFOKNNWNW-UHFFFAOYAF
SMILES C1C=CS1
Properties
Chemical formula	C3H4S
Molar mass	72.12886
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Structure

Thiete is a valence isomer of the compound thioacrolein (CH₂=CHCH=S) and undergoes ring opening to it at temperatures below 400 °C.^[5] Thiete has been shown to be planar, with a C-S-C angle of 76.8 degrees.^[6]

Derivatives

Benzothietes are thietes annulated to benzo group. Such species are prepared by flash vacuum pyrolysis of 2-mercaptobenzyl alcohols. They are precursors to other S-heterocycles.^[7]

Thiete 1,1-dioxides are sulfones, the parent being C₃H₄SO₂. They are more stable than the parent thietes.^[8] Substituted thiete-1,1-dioxides can also be prepared by [2+2] cycloaddition of sulfenes and ynamines.

See also

• Dithiete - analogue with two sulfur atoms