Dithiolane
Encyclopedia
A dithiolane is a sulfur
heterocycle
derived from cyclopentane
by replacing two CH2
groups 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 group
s 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.
Sulfur
Sulfur or sulphur is the chemical element with atomic number 16. In the periodic table it is represented by the symbol S. It is an abundant, multivalent non-metal. Under normal conditions, sulfur atoms form cyclic octatomic molecules with chemical formula S8. Elemental sulfur is a bright yellow...
heterocycle
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
derived from cyclopentane
Cyclopentane
Cyclopentane is a highly flammable alicyclic hydrocarbon with chemical formula 510 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It occurs as a colorless liquid with a petrol-like odor. Its melting point is −94 °C...
by replacing two CH2
Methylene
Methylene is a chemical species in which a carbon atom is bonded to two hydrogen atoms. Three different possibilities present themselves:* the -CH2- substituent group: e.g., dichloromethane ....
groups with thioether
Thioether
A thioether is a functional group in organosulfur chemistry with the connectivity C-S-C as shown on right. Like many other sulfur-containing compounds, volatile thioethers have foul odors. A thioether is similar to an ether except that it contains a sulfur atom in place of the oxygen...
groups. The parent compounds are 1,2-dithiolane and 1,3-dithiolane.
1,2-Dithiolanes, such as lipoic acid
Lipoic acid
Lipoic acid , also known as α-lipoic acid and Alpha Lipoic Acid is an organosulfur compound derived from octanoic acid. LA contains two vicinal sulfur atoms attached via a disulfide bond and is thus considered to be oxidized...
, are cyclic disulfides.
1,3-Dithiolanes are important as protecting group
Protecting group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction...
s for carbonyl
Carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups....
compounds, since they are inert to a wide range of conditions. Reacting a carbonyl group with 1,2-ethanedithiol
1,2-Ethanedithiol
1,2-Ethanedithiol is a colorless liquid with the formula C2H42. It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in organic synthesis and an excellent ligand for metal ions.-Preparation:...
converts it to a 1,3-dithiolane, as detailed below.