Dithiane

Dithianes

1,2-dithiane (left), 1,3-dithiane and 1,4-dithiane (right)
Names
Other names Dithiacyclohexanes
Identifiers
CAS Number	505-20-4 (1,2-dithiane) 505-23-7 (1,3-dithiane) 505-29-3 (1,4-dithiane)
Jmol 3D model	(1,2-dithiane): Interactive image (1,3-dithiane): Interactive image (1,4-dithiane): Interactive image
PubChem	136335 (1,2-dithiane) 10451 (1,3-dithiane) 10452 (1,4-dithiane)
SMILES (1,2-dithiane): C1CCSSC1 (1,3-dithiane): C1CSCSC1 (1,4-dithiane): C1CSCCS1
Properties
Chemical formula	C4H8S2
Molar mass	120.23 g·mol−1
Vapor pressure	{{{value}}}
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

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. 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:

Corey-Seebach

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

External links

• Corey-Seebach Reaction
• 1,3-Dithianes, 1,3-Dithiolanes

• ;
• T. W. Green, P. G. M. Wuts, "Protective Groups in Organic Synthesis" Wiley-Interscience, New York, 1999. ISBN 978-0-471-69754-1.