# Thiete

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Thiete
> Markdown URL: https://mediated.wiki/source/Thiete.md
> Source: https://en.wikipedia.org/wiki/Thiete
> Source revision: 1354249705
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424960119
| ImageFile=Thietene.png
| ImageSize=100
| PIN=2''H''-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=C<sub>3</sub>H<sub>4</sub>S
| MolarMass=72.12886
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
}}

'''Thiete''' is a [heterocyclic compound](/source/heterocyclic_compound) containing an [unsaturated](/source/Saturated_and_unsaturated_compounds) four-membered ring with three carbon atoms and one sulfur atom.<ref>{{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}}</ref><ref>{{cite journal |last=Block |first=E |title=Thietes and Derivatives |journal =Sci. Synth. |year=2007 |volume=33 |pages=187–202}}</ref><ref name=Encyc>{{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=773&ndash;802|chapter=Thietanes and Thietes: Monocyclic|editor-last2=Rees|editor-first2=Charles W.|editor-last3=Scriven|editor-first3=Eric F. V.}}</ref> It is more commonly encountered not on its own, but in [anellated](/source/Polycyclic_compound) derivatives, several of which have been synthesized. Thietes are generally not very stable.<ref>{{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|bibcode=1965JAChS..87.2064D }}</ref>

== Structure ==
Thiete is a [valence isomer](/source/valence_isomer) of the compound thio[acrolein](/source/acrolein) (CH<sub>2</sub>=CHCH=S) and undergoes ring opening to it when heated at temperatures below 400{{Nbsp}}°C.<ref name=Encyc/>{{rp|780}} Thiete has been shown to be planar, with a C-S-C angle of 76.8 degrees.<ref>{{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 }}</ref>

In principle, deprotonation should give a cyclic, planar anion with 6 π electrons, satisfying the [Hückel criteria](/source/H%C3%BCckel's_rule) for [aromaticity](/source/aromatic_(chemistry)).  Computer simulations in 1965 suggested that any aromatic stabilization was small, and other known [approximation error](/source/approximation_error)s likely increased the instability.  Certainly, attempts at deprotonation give only an uncharacterized mixture of decomposition products or [nucleophilic substitution](/source/nucleophilic_substitution), even with relatively [hindered base](/source/hindered_base)s.<ref name=Rev>{{cite book|pp=513&ndash;514, 522&ndash;523|doi=10.1002/9780470187203|title=Small Ring Heterocycles|volume=3|chapter=Four-membered sulfur heterocycles|first1=D. C.|last1=Dittmer|first2=T. C.|last2=Sedergran|series=Chemistry of Heterocyclic Compounds|year=1985|publisher=Wiley|isbn=9780471056249}}</ref>

==Derivatives==
Benzothietes are thietes annulated to benzo group.  Such species are prepared by [flash vacuum pyrolysis](/source/flash_vacuum_pyrolysis) of 2-mercapto[benzyl alcohol](/source/benzyl_alcohol)s. They are precursors to other S-heterocycles.<ref>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}}</ref>

Thiete 1,1-dioxides are [sulfone](/source/sulfone)s, the parent being C<sub>3</sub>H<sub>4</sub>SO<sub>2</sub>. They are more stable than the parent thietes.<ref>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}}</ref> Substituted thiete-1,1-dioxides can be prepared through oxidation of thietes, elimination of thietane dioxides, or [2+2] [cycloaddition](/source/cycloaddition) of [sulfene](/source/sulfene)s and ynamines.<ref name=Rev/>{{rp|pp=531-535}}

== See also ==

* [Dithiete](/source/Dithiete) - analogue with two sulfur atoms

== References ==
{{Reflist}}

Category:Sulfur heterocycles
Category:Four-membered rings

---
Adapted from the Wikipedia article [Thiete](https://en.wikipedia.org/wiki/Thiete) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Thiete?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.