1,3-Dithiolane
Chemical compound
From Wikipedia, the free encyclopedia
1,3-Dithiolane is the organosulfur compound with the formula CH2S2C2H4. Also classified as a heterocycle related cyclopentane by replacing two methylene bridges (âCH2â units) with thioether groups. It is an isomer of 1,2-dithiolane.[1] 1,3-Dithiolanes are compounds where one or more H atoms of the parent 1,3-dithiolane are replaced by other groups. These species are more widely studied.
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| Names | |||
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| Preferred IUPAC name
1,3-Dithiolane | |||
| Identifiers | |||
3D model (JSmol) |
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| 102455 | |||
| ChEBI | |||
| ChemSpider | |||
| 82036 | |||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| C3H6S2 | |||
| Molar mass | 106.20 g·molâ1 | ||
| Related compounds | |||
Related compounds |
Ethane-1,2-dithiol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
A common family of 1,3-dithiolanes have the formula RCHS2C2H4. They are obtained by treating an aldehyde with 1,2-ethanedithiol.[2] Related compounds with the formula R2CS2C2H4 are obtained by condensation of 1,2-ethanedithiol with ketones.[3] The dithiolane protected aldehydes and ketones are amenable to many reactions without perturbing the dithiolane ring.[4]
Dithiolanes can often be reverted, i.e., deprotected,[5] to the parent aldehyde and ketone. A variety of reagents have been developed for that purpose.[6]
Reactions
1,3-Dithiolanes derived from aldehydes can be deprotonated:
- RCHS2C2H4 + BuLi â RCLiS2C2H4 + BuH
These organolithium compounds degrade with loss of ethylene to give the dithiocarboxylate:
- RCLiS2C2H4 â RCS2Li + C2H4
In contrast, 2-lithio-1,3-dithianes (RCLiS2C3H6) are long-lived.
1,3-Dithiolanes are susceptible to a variety of degradation processes involving organometallic reagents leading to other organosulfur compounds.[2][3]
