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Chemical compound From Wikipedia, the free encyclopedia
A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges (-CH
2- 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 (left), 1,3-dithiane and 1,4-dithiane (right) | |
Names | |
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Other names
Dithiacyclohexanes | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
PubChem CID |
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Properties | |
C4H8S2 | |
Molar mass | 120.23 g·mol−1 |
Melting point | 32.5 °C (90.5 °F; 305.6 K) other isomers: 54 (1,3), 112.3 (1,4) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,2-Dithiane is an organosulfur compound with the formula S2C4H8. It is one of three isomers of the formula (CH2)4S2. The 1,2-isomer, a disulfide, arises by the oxidation of 1,4-butanedithiol.
1,3-Dithiane is an organosulfur compound with the formula CH2S2C3H6. It is one of three isomers of the formula (CH2)4S2. The 1,3-isomer arises by the reaction of 1,3-propanedithiol with formaldehyde.[1]
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:[2]
1,4-Dithiane is an organosulfur compound with the formula (SC2H4)2. It is one of three isomers of the formula (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[3] coal pyrolysis.[4]
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