dithiane
{{Chembox
| Name = Dithianes
| ImageFile = DithianeOverviewBW.svg
| ImageCaption = 1,2-dithiane (left), 1,3-dithiane and 1,4-dithiane (right)
| IUPACName =
| OtherNames = Dithiacyclohexanes
|Section1={{Chembox Identifiers
| index_label=1,2-dithiane
| index1_label=1,3-dithiane
| index2_label=1,4-dithiane
| CASNo = 505-20-4
| CASNo1 = 505-23-7
| CASNo2 = 505-29-3
| PubChem = 136335
| PubChem1 = 10451
| PubChem2 = 10452
| SMILES = C1CCSSC1
| SMILES1 = C1CSCSC1
| SMILES2 = C1CSCCS1
| ChemSpiderID = 120109
| InChI = 1S/C4H8S2/c1-2-4-6-5-3-1/h1-4H2
| InChIKey = CXWGKAYMVASWDQ-UHFFFAOYSA-N
| ChemSpiderID1 = 10019
| InChI1 = 1S/C4H8S2/c1-2-5-4-6-3-1/h1-4H2
| InChIKey1 = WQADWIOXOXRPLN-UHFFFAOYSA-N
| ChemSpiderID2 = 10020
| InChI2 = 1S/C4H8S2/c1-2-6-4-3-5-1/h1-4H2
| InChIKey2 = LOZWAPSEEHRYPG-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=4 | H=8 | S=2
| Appearance =
| Density =
| MeltingPtC = 32.5
| MeltingPt_notes = other isomers: 54 (1,3), 112.3 (1,4)
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges ({{chem2|\sCH2\s}} units) are replaced by sulfur. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane. They are all colorless solids.
{{Multiple image|align=left| footer = Space filling models of 1,2-dithiane (left), 1,3-dithiane and 1,4-dithiane (right) | direction =horizontal | image1 = Dithiane23d.png |image2 = Dithiane13d.png |image3 = Dithiane33d.png | width1 = 100 | width2 = 100 | width3 = 100}}{{clear-left}}
1,2-Dithiane
1,2-Dithiane is an organosulfur compound with the formula {{chem2|S2C4H8}}. It is one of three isomers of the formula {{chem2|(CH2)4S2}}. The 1,2-isomer, a disulfide, arises by the oxidation of 1,4-butanedithiol.
1,3-Dithiane
1,3-Dithiane is an organosulfur compound with the formula {{chem2|CH2S2C3H6}}. It is one of three isomers of the formula {{chem2|(CH2)4S2}}. The 1,3-isomer arises by the reaction of 1,3-propanedithiol with formaldehyde.{{OrgSynth
| first1 = E. J.
|last1 =Corey
|first2=D
|last2= Seebach
| year = 1970
| title = 1,3-Dithiane
| volume =50
| page =72
| doi = 10.15227/orgsyn.050.0072
| collvol =
| collvolpages =
| prep =}}
1,3-Dithianes are sometimes used as protecting group of carbonyl-containing compounds. They form by treatment of the carbonyl compound with 1,3-propanedithiol under conditions that remove water from the system. The protecting group can be removed with mercuric reagents, a process that exploits the high affinity of Hg(II) for thiolates. 1,3-Dithianes are more importantly employed in umpolung reactions, such as the Corey–Seebach reaction:{{cite book|last1=Wuts|first1=P. G. M.|last2=Greene, T.W.|year=2006|title=Greene's Protective Groups in Organic Synthesis|doi=10.1002/0470053488|isbn= 9780470053485|publisher=J. Wiley|location=NY|s2cid=83393227 }}
1,4-Dithiane
1,4-Dithiane is an organosulfur compound with the formula {{chem2|(SC2H4)2}}. It is one of three isomers of the formula {{chem2|(CH2)4S2}}. The 1,4-isomer, a bisthioether, arises by the alkylation of 1,2-ethanedithiol with 1,2-dibromoethane. It has no applications but traces occur as a product of degradations, e.g., cooking{{cite journal |last1=Garbusov |first1=V. |last2=Rehfeld |first2=G. |last3=Wölm |first3=G. |last4=Golovnja |first4=R. V. |last5=Rothe |first5=M. |title=Volatile sulfur compounds contributing to meat flavour. Part. I. Components identified in boiled meat |journal=Molecular Nutrition & Food Research |date=1976 |volume=20 |issue=3 |pages=235–241 |doi=10.1002/food.19760200302|pmid=958341 }} coal pyrolysis.{{cite journal |last1=Calkins |first1=William H. |title=Investigation of organic sulfur-containing structures in coal by flash pyrolysis experiments |journal=Energy Fuels |date=1987 |volume=1 |issue=1 |pages=59–64 |doi=10.1021/ef00001a011}}
References
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