Dithiane

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Dithianes
DithianeOverview.svg
1,2-dithiane (left), 1,3-dithiane and 1,4-dithiane (right)
Names
Other names
Dithiacyclohexanes
Identifiers
3D model (JSmol)
ChemSpider
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

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)

1,3-Dithianes[edit]

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]

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

References[edit]

  1. ^ E. J. Corey, D. Seebach (1988). "1,3-Dithiane". Org. Synth. ; Coll. 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.

External links[edit]