A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting groups of carbonyl groups, making them essential in synthesis of organic chemistry.
In organosulfur chemistry, thioacetals are the sulfur (thio-) analogues of acetals. There are two classes: the less-common monothioacetals, with the formula R−CH(−OR')−SR", and the dithioacetals, with the formula R−CH(−SR')2 or R−CH(−SR')−SR".
Asparagusic acid is an organosulfur compound with the molecular formula C4H6O2S2 and systematically named 1,2-dithiolane-4-carboxylic acid. The molecule consists of a heterocyclic disulfide functional group (a 1,2-dithiolane) with a carboxylic acid side chain. It is found in asparagus and is believed to be the metabolic precursor to odorous sulfur compounds responsible for the distinctive smell of urine which has long been associated with eating asparagus.
The Gabriel–Colman rearrangement is the chemical reaction of a saccharin or phthalimido ester with a strong base, such as an alkoxide, to form substituted isoquinolines. First described in 1900 by chemists Siegmund Gabriel and James Colman, this rearrangement, a ring expansion, is seen to be general if there is an enolizable hydrogen on the group attached to the nitrogen, since it is necessary for the nitrogen to abstract a hydrogen to form the carbanion that will close the ring. As shown in the case of the general example below, X is either CO or SO2.
Ethane-1,2-dithiol, also known as EDT, is a colorless liquid with the formula C2H4(SH)2. It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in organic synthesis and an excellent ligand for metal ions.
A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges are replaced by sulfur. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane. They are all colorless solids.
1,3-Propanedithiol is the chemical compound with the formula HSCH2CH2CH2SH. This dithiol is a useful reagent in organic synthesis. This liquid, which is readily available commercially, has an intense stench.
In enzymology, a thiosulfate-dithiol sulfurtransferase is an enzyme that catalyzes the chemical reaction
Dithiete is an unsaturated heterocyclic compound that contains two adjacent sulfur atoms and two sp2-hybridized carbon centers. Derivatives are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of aromatic organosulfur compounds. A few 1,2-dithietes have been isolated; one (low-yielding) route is oxidation of a dithiolene complex. 3,4-Bis(trifluoromethyl)-1,2-dithiete is a particularly stable example.
Luche reduction is the selective organic reduction of α,β-unsaturated ketones to allylic alcohols. The active reductant is described as "cerium borohydride", which is generated in situ from NaBH4 and CeCl3(H2O)7.
Benzene-1,2-dithiol is the organosulfur compound with the formula C6H4(SH)2. This colourless viscous liquid consists of a benzene ring with a pair of adjacent thiol groups. The conjugate base of this diprotic compound serves as chelating agent in coordination chemistry and a building block for the synthesis of other organosulfur compounds.
1,2-Dithietane is a dithietane. It is a heterocyclic compound with a four-membered ring. Two sulfur atoms are adjacent, and the molecule is saturated. 1,2-Dithietane has not been produced as of 2000. The combination of ring strain, and lone pairs of electrons, which repel each other, on the sulfur atoms makes the sulfur-sulfur bond too weak to produce the molecule. However a few derivatives are known. 3,4-Diethyl-1,2-dithietane 1,1-dioxide has one sulfur fully oxidised. Dithiatopazine is a tricyclic compound with the -S-S- as a bridge. 1,2-Dithietan-3-one, the ketone of 1,2-dithietane, was produced in 2008 by reacting α-dithiolactone with ethoxycarbonylformonitrile oxide. 4,4-di-tert-butyl-1,2-dithietan-3-one and the spiro compound 5,5,9,9-tetramethyl-1,2-dithiaspiro[3.5]nonan-3-one have also been made.
The thiol-yne reaction is an organic reaction between a thiol and an alkyne. The reaction product is an alkenyl sulfide. The reaction was first reported in 1949 with thioacetic acid as reagent and rediscovered in 2009. It is used in click chemistry and in polymerization, especially with dendrimers.
In organic chemistry, a dithiol is a type of organosulfur compound with two thiol functional groups. Their properties are generally similar to those of monothiols in terms of solubility, odor, and volatility. They can be classified according to the relative location of the two thiol groups on the organic backbone.
Ethane-1,1-dithiol is an organosulfur compound with formula CH3CH(SH)2. It is a colourless smelly liquid that is added to or found in some foods. The compound is an example of a geminal dithiol.
The Corey–Seebach reaction, or Seebach Umpolung is a name reaction of organic chemistry that allows for acylation by converting aldehydes into lithiated 1,3-dithianes. The lithiated 1,3-dithianes serves as an acyl anion equivalent, undergoing alkylation with electrophiles. The reaction is named in honor of its discoverers, Elias J. Corey and Dieter Seebach.
Nereistoxin is a natural product identified in 1962 as the toxic organic compound N,N-dimethyl-1,2-dithiolan-4-amine. It had first been isolated in 1934 from the marine annelid Lumbriconereis heteropoda and acts by blocking the nicotinic acetylcholine receptor. Researchers at Takeda in Japan investigated it as a possible insecticide. They subsequently developed a number of derivatives that were commercialised, including those with the ISO common names bensultap, cartap, thiocyclam and thiosultap.
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 with a disulfide group. 1,3-Dithiolane is an isomer. The parent molecule is not important but substituted derivatives, especially lipoic acid and its derivatives, are important. Several occur in foods.
1,4-Butanedithiol is an organosulfur compound with the formula HSCH2CH2CH2CH2SH. It is a malodorous, colorless liquid that is highly soluble in organic solvents. The compound has found applications in biodegradable polymers.
3,4-Toluenedithiol is an organosulfur compound with the formula CH3C6H3(SH)2. It is encountered as a colorless wax or oil. The compound is classified as an aromatic dithiol. It forms brightly colored derivatives with many metal ions. The compound is closely related to 1,2-benzenedithiol but is often more widely used because it is less expensive. 3,4-Toluenedithiol is prepared by reduction of the bis(sulfonyl chloride) CH3C6H3(SO2Cl)2 with tin.
