Dithiane Explained

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-Dithianes

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-Dithianes

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.

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]

1,4-Dithianes

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[2] coal pyrolysis.[3]

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Notes and References

  1. Book: Wuts. P. G. M.. Greene, T.W.. 2006. Greene's Protective Groups in Organic Synthesis. 10.1002/0470053488. 9780470053485. J. Wiley. NY. 83393227 .
  2. Garbusov . V. . Rehfeld . G. . Wölm . G. . Golovnja . R. V. . Rothe . M. . Volatile sulfur compounds contributing to meat flavour. Part. I. Components identified in boiled meat . Molecular Nutrition & Food Research . 1976 . 20 . 3 . 235–241 . 10.1002/food.19760200302.
  3. Calkins . William H. . Investigation of organic sulfur-containing structures in coal by flash pyrolysis experiments . Energy Fuels . 1987 . 1 . 1 . 59–64 . 10.1021/ef00001a011.