Dithiolane
Appearance
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Names | |||
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IUPAC name
Dithiolane
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Other names
1,2-dithiolane, 1,3-dithiolane
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Identifiers | |||
3D model (JSmol)
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ChEBI | |||
ChemSpider | |||
PubChem CID
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Properties | |||
C3H6S2 | |||
Related compounds | |||
Related compounds
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1,2-Ethanedithiol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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A dithiolane is a sulfur heterocycle derived from cyclopentane by replacing two methylene bridges (-CH
2- units) with thioether groups. The parent compounds are 1,2-dithiolane and 1,3-dithiolane.
1,2-Dithiolanes, such as lipoic acid, are cyclic disulfides.
1,3-Dithiolanes are important as protecting groups for carbonyl compounds, since they are inert to a wide range of conditions. Reacting a carbonyl group with 1,2-ethanedithiol converts it to a 1,3-dithiolane, as detailed below.
![Protecting a carbonyl group by converting it to a 1,3-dithiolane, using 1,2-ethanedithiol](http://upload.wikimedia.org/wikipedia/commons/thumb/0/00/Carbonyl-protection-with-ethanedithiol-2D.png/400px-Carbonyl-protection-with-ethanedithiol-2D.png)
A dithiolanone is a dithiolane which is also a ketone.