Thiirene

Last updated
Thiirene
Thiiren.png
Names
Preferred IUPAC name
Thiirene
Systematic IUPAC name
Thiacyclopropene
Other names
Epithioethene
Ethyne sulfide
Acetylene sulfide
Identifiers
3D model (JSmol)
1304471
ChEBI
ChemSpider
239545
PubChem CID
  • InChI=1S/C2H2S/c1-2-3-1/h1-2H X mark.svgN
    Key: JTQAPFZZCXWQNQ-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C2H2S/c1-2-3-1/h1-2H
    Key: JTQAPFZZCXWQNQ-UHFFFAOYAN
  • C1=CS1
Properties
C2H2S
Molar mass 58.10228
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thiirene is an organosulfur compound with the formula C2H2S. It can be viewed as a derivative of cyclopropene, but with the methylene group replaced by sulfur. It is antiaromatic and very labile. [1]

Thiirenes and derivatives

No thiirene has been isolated at room temperature, but they have been observed spectroscopically at low temperatures. [2]

Thiirene-S-oxides and S-alkylthiirenium salts have been characterized by X-ray crystallography. [3]

Related Research Articles

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3
, methanium CH+
5
and vinyl C
2
H+
3
cations. Occasionally, carbocations that bear more than one positively charged carbon atom are also encountered.

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<span class="mw-page-title-main">Silabenzene</span> Chemical compound

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<span class="mw-page-title-main">Corey–Itsuno reduction</span>

The Corey–Itsuno reduction, also known as the Corey–Bakshi–Shibata (CBS) reduction, is a chemical reaction in which a prochiral ketone is enantioselectively reduced to produce the corresponding chiral, non-racemic alcohol. The oxazaborolidine reagent which mediates the enantioselective reduction of ketones was previously developed by the laboratory of Itsuno and thus this transformation may more properly be called the Itsuno-Corey oxazaborolidine reduction.

<span class="mw-page-title-main">Trimyristin</span> Chemical compound

Trimyristin is a saturated fat and the triglyceride of myristic acid with the chemical formula C45H86O6. Trimyristin is a white to yellowish-gray solid that is insoluble in water, but soluble in ethanol, acetone, benzene, chloroform, dichloromethane, ether, and TBME.

<span class="mw-page-title-main">Corannulene</span> Chemical compound

Corannulene is a polycyclic aromatic hydrocarbon with chemical formula C20H10. The molecule consists of a cyclopentane ring fused with 5 benzene rings, so another name for it is [5]circulene. It is of scientific interest because it is a geodesic polyarene and can be considered a fragment of buckminsterfullerene. Due to this connection and also its bowl shape, corannulene is also known as a buckybowl. Buckybowls are fragments of buckyballs. Corannulene exhibits a bowl-to-bowl inversion with an inversion barrier of 10.2 kcal/mol (42.7 kJ/mol) at −64 °C.

<span class="mw-page-title-main">Halonium ion</span> Any onium ion containing a halogen atom carrying a positive charge

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<span class="mw-page-title-main">Methyllithium</span> Chemical compound

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<span class="mw-page-title-main">Sandwich compound</span> Chemical compound made of two ring ligands bound to a metal

In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by haptic, covalent bonds to two arene (ring) ligands. The arenes have the formula CnHn, substituted derivatives and heterocyclic derivatives. Because the metal is usually situated between the two rings, it is said to be "sandwiched". A special class of sandwich complexes are the metallocenes.

<span class="mw-page-title-main">Fullerene chemistry</span>

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<span class="mw-page-title-main">Group 2 organometallic chemistry</span>

Group 2 organometallic chemistry refers to the chemistry of compounds containing carbon bonded to any group 2 element. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organometallic group 2 compounds are rare and are typically limited to academic interests.

<span class="mw-page-title-main">Dioxirane</span> Chemical compound

In chemistry, dioxirane is an organic compound with formula CH
2
O
2
. The molecule consists of a ring with one methylene and two oxygen atoms. It is of interest as the smallest cyclic organic peroxide, but otherwise it is of little practical value.

<span class="mw-page-title-main">Magnesium hydride</span> Chemical compound

Magnesium hydride is the chemical compound with the molecular formula MgH2. It contains 7.66% by weight of hydrogen and has been studied as a potential hydrogen storage medium.

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<span class="mw-page-title-main">Mixed-valence complex</span> Type of chemical compound

Mixed valence complexes contain an element which is present in more than one oxidation state. Well-known mixed valence compounds include the Creutz–Taube complex, Prussian blue, and molybdenum blue. Many solids are mixed-valency including indium chalcogenides.

References

  1. Ando, Wataru; Choi, Nami; Tokitoh, Norihiro (1996). "Thiiranes and Thiirenes: Monocyclic". Comprehensive Heterocyclic Chemistry II. pp. 173–240. doi:10.1016/B978-008096518-5.00005-8. ISBN   9780080965185.
  2. Torres, M.; Clement, A.; Bertie, J. E.; Gunning, H. E.; Strausz, O. P. (1978). "Low-Temperature Matrix Isolation of Thiirenes". The Journal of Organic Chemistry. 43 (12): 2490–2493. doi:10.1021/jo00406a045.
  3. Destro, Riccardo; Lucchini, Vittorio; Modena, Giorgio; Pasquato, Lucia (2000). "X-ray Structures and Anionotropic Rearrangements of Di-tert-butyl-Substituted Thiiranium and Thiirenium Ions. A Structure−Reactivity Relationship". The Journal of Organic Chemistry. 65 (11): 3367–3370. doi:10.1021/jo991731o. PMID   10843618.