Dithiane

A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges (-CH
2- units) are replaced by sulfur centres. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane.

Space filling models of 1,2-dithiane (left), 1,3-dithiane and 1,4-dithiane (right)
Dithianes

1,2-dithiane (left), 1,3-dithiane and 1,4-dithiane (right)
Names
Other names
Dithiacyclohexanes
Identifiers
3D model (JSmol)
ChemSpider
  • 1,2-dithiane: InChI=1S/C4H8S2/c1-2-4-6-5-3-1/h1-4H2
    Key: CXWGKAYMVASWDQ-UHFFFAOYSA-N
  • 1,3-dithiane: InChI=1S/C4H8S2/c1-2-5-4-6-3-1/h1-4H2
    Key: WQADWIOXOXRPLN-UHFFFAOYSA-N
  • 1,4-dithiane: InChI=1S/C4H8S2/c1-2-6-4-3-5-1/h1-4H2
    Key: LOZWAPSEEHRYPG-UHFFFAOYSA-N
  • 1,2-dithiane: C1CCSSC1
  • 1,3-dithiane: C1CSCSC1
  • 1,4-dithiane: C1CSCCS1
Properties
C4H8S2
Molar mass 120.23 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,3-Dithianes

1,3-Dithianes are protecting group of some carbonyl-containing compounds due to their inertness to many conditions. They form by treatment of the carbonyl compound with 1,3-propanedithiol under conditions that remove water from the system.[1] 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 also employed in umpolung reactions, such as the Corey–Seebach reaction:[2]

Umpolung reactions with 1,3-dithianes

Typically, in organic synthesis, ketones and aldehydes are protected as their dioxolanes instead of dithianes.

References
  1. E. J. Corey, D. Seebach (1988). "1,3-Dithiane". Organic Syntheses.; Collective Volume, vol. 6, p. 556
  2. T. W. Green, P. G. M. Wuts, "Protective Groups in Organic Synthesis" Wiley-Interscience, New York, 1999. ISBN 978-0-471-69754-1.
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