1,3-Dithiolane is the

organosulfur Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...

compound with the formula . Also classified as a

heterocycle A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

cyclopentane Cyclopentane (also called C pentane) is a highly flammable alicyclic compound, alicyclic hydrocarbon with chemical formula C5H10, C5H10 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and ...

by replacing two

methylene bridge In chemistry, a methylene bridge is part of a molecule with formula . The carbon atom is connected by single bonds to two other distinct atoms in the rest of the molecule. A methylene bridge is often called a methylene group or simply methylene, ...

s ( units) with

thioether In organic chemistry, a sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity as shown on right. Like many other sulfur-containing compounds, Volatile organic compound, volatile sulfides have ...

groups. It is an isomer of

1,2-dithiolane 1,2-Dithiolane is an organosulfur compound with the formula . It is also classified as a heterocycle derived from cyclopentane by replacing two methylene bridges ( units) with a disulfide group. 1,3-Dithiolane is an isomer. The parent molecule ...

. 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.

Synthesis

A common family of 1,3-dithiolanes have the formula . They are obtained by treating an

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

with 1,2-ethanedithiol. Related compounds with the formula are obtained by condensation of 1,2-ethanedithiol with

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

s. The dithiolane protected aldehydes and ketones are amenable to many reactions without perturbing the dithiolane ring. Carbonyl-protection-with-ethanedithiol-2D

Carbonyl-protection-with-ethanedithiol-2D

Dithiolanes can often be reverted, i.e., deprotected, to the parent aldehyde and ketone. A variety of reagents have been developed for that purpose.

Reactions

1,3-Dithiolanes derived from aldehydes can be deprotonated: : These organolithium compounds degrade with loss of ethylene to give the

dithiocarboxylate Dithiocarboxylic acids are organosulfur compounds with the formula . They are the dithia analogues of carboxylic acids. A closely related and better studied family of compounds are the monothiocarboxylic acids, with the formula . Dithiocarboxyli ...

: : In contrast, 2-lithio-1,3-dithianes () are long-lived. 1,3-Dithiolanes are susceptible to a variety of degradation processes involving organometallic reagents leading to other organosulfur compounds.

References

External links

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1,3-Dithiolane Reactions