Dithiane

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title: "Dithiane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["dithianes"] topic_path: "general/dithianes" source: "https://en.wikipedia.org/wiki/Dithiane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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 ( 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.

1,2-Dithiane

1,2-Dithiane is an organosulfur compound with the formula . It is one of three isomers of the formula . 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 . It is one of three isomers of the formula . 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:

1,4-Dithiane

1,4-Dithiane is an organosulfur compound with the formula . It is one of three isomers of the formula . 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 coal pyrolysis.

References

References

  1. (2006). "Greene's Protective Groups in Organic Synthesis". J. Wiley.
  2. (1976). "Volatile sulfur compounds contributing to meat flavour. Part. I. Components identified in boiled meat". Molecular Nutrition & Food Research.
  3. (1987). "Investigation of organic sulfur-containing structures in coal by flash pyrolysis experiments". Energy Fuels.

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dithianes