A dithiolane is a

sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...

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

derived from

cyclopentane Cyclopentane (also called C pentane) is a highly flammable alicyclic hydrocarbon with chemical formula C5H10 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 occur ...

by replacing two

methylene bridge In organic chemistry, a methylene bridge, methylene spacer, or methanediyl group is any part of a molecule with formula ; namely, a carbon atom bound to two hydrogen atoms and connected by single bonds to two other distinct atoms in the rest of ...

s (-- units) with

thioether In organic chemistry, an organic 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 sulfides have foul odors. A sul ...

groups. The parent compounds are 1,2-dithiolane and 1,3-dithiolane. 1,2-Dithiolanes are cyclic

disulfides In biochemistry, a disulfide (or disulphide in British English) refers to a functional group with the structure . The linkage is also called an SS-bond or sometimes a disulfide bridge and is usually derived by the coupling of two thiol groups. In ...

. Some dithiolanes are

natural products A natural product is a natural Chemical compound, compound or chemical substance, substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural product ...

that can be found in foods, such as

asparagusic acid Asparagusic acid is an organosulfur compound with the molecular formula C4H6O2S2 and IUPAC nomenclature of organic chemistry, systematically named 1,2-dithiolane-4-carboxylic acid. The molecule consists of a heterocyclic disulfide functional gr ...

in asparagus. The 4-dimethylamino derivative nereistoxin was the inspiration for

insecticides Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...

which act by blocking the

nicotinic acetylcholine receptor Nicotinic acetylcholine receptors, or nAChRs, are receptor polypeptides that respond to the neurotransmitter acetylcholine. Nicotinic receptors also respond to drugs such as the agonist nicotine. They are found in the central and peripheral ne ...

Lipoic acid Lipoic acid (LA), also known as α-lipoic acid, alpha-lipoic acid (ALA) and thioctic acid, is an organosulfur compound derived from caprylic acid (octanoic acid). ALA is made in animals normally, and is essential for aerobic metabolism. It is a ...

is essential for

aerobic metabolism Cellular respiration is the process by which biological fuels are oxidised in the presence of an inorganic electron acceptor such as oxygen to produce large amounts of energy, to drive the bulk production of ATP. Cellular respiration may be des ...

in mammals and also has strong affinity with many metals including gold, molybdenum, and tungsten. Other 1,2-dithiolanes have relevance in nanomaterials such as gold nanoparticles or

transition metal dichalcogenide monolayers Transition-metal dichalcogenide (TMD or TMDC) monolayers are atomically thin semiconductors of the type MX2, with M a transition-metal atom ( Mo, W, etc.) and X a chalcogen atom ( S, Se, or Te). One layer of M atoms is sandwiched between two ...

(TMDs) ( MoS₂ and WS₂). Asparagusic-acid.png, asparagusic acid Nereistoxin.svg, nereistoxin, from which insecticides including cartap and bensultap were derived Lipoic acid.svg, lipoic acid 1,3-Dithiolanes are important as

protecting group A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many ...

s for

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. A compound containing a ...

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. Carbonyl-protection-with-ethanedithiol-2D

Carbonyl-protection-with-ethanedithiol-2D

References

External links

*{{Commons category-inline, Dithiolanes
1,3-Dithiolane Reactions