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1,2-Dithiolane
Chemical compound From Wikipedia, the free encyclopedia
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1,2-Dithiolane is an organosulfur compound with the formula S2(CH2)3. It is also classified as a heterocycle derived from cyclopentane by replacing two methylene bridges (−CH2− units) with a disulfide group. 1,3-Dithiolane is an isomer. The parent molecule is unimportant but substituted derivatives, especially lipoic acid and its derivatives, are often essential for life. Several occur naturally.[1]
The parent 1,2-dithiolane is the disulfide derived from 1,3-propanedithiol. It is however unstable with respect to oligomerization.[2] In general, 1,3-dithiols are superior reductants relative to monothiols.[3]
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Natural occurrence
Many substituted 1,2-dithiolates are found in nature.[4] The most common is lipoic acid, a chiral dithiolane, which features a pentanoic acid substituent. It is essential for aerobic metabolism in mammals.
Some 1,2-dithiolane are found in some foods, such as asparagusic acid in asparagus.[5] The 4-dimethylamino derivative nereistoxin was the inspiration for insecticides that act by blocking the nicotinic acetylcholine receptor.[6]
Several alkyl-substituted 1,2-dithiolanes occur in the scent glands of skunks and related mammals. These include 3,3-dimethyl-, 3-propyl-, 3-ethyl-1,2-dithiolane, and others.[4]
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Dithiolane-S-oxides

Many 1,2-dithiolanes can be oxidized to their S-oxides, which are chiral.[4]
References
External links
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