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1,3-Dithiolane

Chemical compound From Wikipedia, the free encyclopedia

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1,3-Dithiolane is the organosulfur compound with the formula CH2S2C2H4. Also classified as a heterocycle related cyclopentane by replacing two methylene bridges (−CH2 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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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]

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

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]

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Reactions

1,3-Dithiolanes derived from aldehydes can be deprotonated:

RCHS2C2H4 + BuLi → RCLiS2C2H4 + BuH

These organolithium compounds degrade with loss of ethylene to give the dithiocarboxylate:

RCLiS2C2H4 → 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]

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References

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