Thiete
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424960119
| ImageFile=Thietene.png
| ImageSize=100
| PIN=2H-Thiete
| OtherNames=1-Thiacyclobut-2-ene
|Section1={{Chembox Identifiers
| CASNo=503-31-1
| PubChem=3415867
| SMILES=C1C=CS1
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 2659702
| InChI = 1/C3H4S/c1-2-4-3-1/h1-2H,3H2
| InChIKey = HPINPCFOKNNWNW-UHFFFAOYAF
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C3H4S/c1-2-4-3-1/h1-2H,3H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = HPINPCFOKNNWNW-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula=C3H4S
| MolarMass=72.12886
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
}}
Thiete is a heterocyclic compound containing an unsaturated four-membered ring with three carbon atoms and one sulfur atom.{{cite journal |last= Leśniak |first=S |author2=Lewkowski, J |author3=Kudelska, W |author4= Zając, A | title =Thietanes and Thietes: Monocyclic |journal =Comprehensive Heterocyclic Chemistry III |year=2008 |volume=2 |issue=7 |pages=389–428 |doi=10.1016/B978-008044992-0.00207-8}}{{cite journal |last=Block |first=E |title=Thietes and Derivatives |journal =Sci. Synth. |year=2007 |volume=33 |pages=187–202}}{{cite journal |last=Block |first=E |author2=DeWang, M| title =Thietanes and Thietes: Monocyclic |journal =Comprehensive Heterocyclic Chemistry II |year=1996 |volume=1 |issue=24 |pages=773–802 |doi=10.1016/B978-008096518-5.00024-1}} 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.{{cite journal |last=Dittmer|first=DC|author2=Davis, FA| title=Evidence for a Thiete (Thiacyclobutene) |journal =J. Am. Chem. Soc.|year=1965 |volume=87|issue=9 |pages=2064–2065 |doi=10.1021/ja01087a048}}
Structure
Thiete is a valence isomer of the compound thioacrolein (CH2=CHCH=S) and undergoes ring opening to it at temperatures below 400{{Nbsp}}°C.{{Cite book|last1=Block|first1=Eric|title=Comprehensive Heterocyclic Chemistry II|last2=Wang|first2=Ming De|publisher=Elsevier|year=1996|isbn=978-0-08-096518-5|editor-last=Katritzky|editor-first=Alan R.|edition=2nd|volume=1B|pages=780|chapter=Thietanes and Thietes: Monocyclic|editor-last2=Rees|editor-first2=Charles W.|editor-last3=Scriven|editor-first3=Eric F. V.}} Thiete has been shown to be planar, with a C-S-C angle of 76.8 degrees.{{cite journal |last=Rodler |first=M |author2=Bauder, A |title =Microwave spectrum, dipole moment and molecular structure of 1,2-dithiete|journal =Chemical Physics Letters|year=1985 |volume=114 |issue=5–6 |pages=575–578 |doi=10.1016/0009-2614(85)85145-9|bibcode=1985CPL...114..575R }}
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.Herbert Meier, Axel Mayer, Dieter Gröschl "Benzothietes—versatile Synthons For The Preparation Of Heterocycles" Sulfur Reports, 1994, volume 16, 23-56, {{doi|10.1080/01961779408048965}}
Thiete 1,1-dioxides are sulfones, the parent being C3H4SO2. They are more stable than the parent thietes.Thomas C. Sedergran and Donald C. Dittmer "Thiete 1,1-dioxide and Chlorothiete 1,1-dioxide" Org. Synth. 1984, vol. 62, 210.{{doi|10.15227/orgsyn.062.0210}} 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