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Dithiolane

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Dithiolane
Names
IUPAC name
Dithiolane
Other names
1,2-dithiolane, 1,3-dithiolane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C3H6S2/c1-2-4-5-3-1/h1-3H2 checkY
    Key: MUZIZEZCKKMZRT-UHFFFAOYSA-N checkY
  • InChI=1/C3H6S2/c1-2-4-5-3-1/h1-3H2
    Key: MUZIZEZCKKMZRT-UHFFFAOYAH
  • S1SCCC1
Properties
C3H6S2
Related compounds
Related compounds
 1,2-Ethanedithiol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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
Protecting a carbonyl group by converting it to a 1,3-dithiolane, using 1,2-ethanedithiol

A dithiolanone is a dithiolane which is also a ketone.

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