1,5-Dithiacyclooctane
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1,5-Dithiacyclooctane
1,5-Dithiacyclooctane (DTCO) is an organosulfur compound with the formula (CHCH)CHS). This cyclic dithioether is a colorless oil that is soluble in polar solvents. It forms a variety of transition metal thioether complexes. DTO can be oxidized to the bicyclic dication. DTCO was first prepared in 4% yield by dialkylation of 1,3-propanedithiol 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. Use in organic synthesis 1,3-Propan ... with 1,3-dibromopropane. References {{DEFAULTSORT:Dithiacyclooctane, 1, 5- Thioethers Chelating agents Sulfur heterocycles Heterocyclic compounds with 1 ring ...
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1,3-Propanedithiol
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. Use in organic synthesis 1,3-Propanedithiol is mainly used for the protection of aldehydes and ketones via their reversible formation of dithianes. A prototypical reaction is its formation of 1,3-dithiane from formaldehyde. The reactivity of this dithiane illustrates the concept of umpolung. Alkylation gives thioethers, e.g. 1,5-dithiacyclooctane. The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives. 1,3-Propanedithiol is used in the synthesis of tiapamil. Use in inorganic synthesis 1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the derivative diiron propanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl: :Fe3(CO)12 + C3H ...
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Organosulfur Compound
Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two ( cysteine and methionine) are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries. Sulfur shares the chalcogen group with oxygen, selenium, and tellurium, and it is expected that organosulfur compounds have similarities with carbon–oxygen, carbon–selenium, and carbon–tellurium compounds. A classical chemical test for the detection of sulfur co ...
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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 sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application. Nomenclature Sulfides are sometimes called thioethers, especially in the old literature. The two organic substituents are indicated by the prefixes. (CH3)2S is called dimethylsulfide. Some sulfides are named by modifying the common name for the corresponding ether. For example, C6H5SCH3 is methyl phenyl sulfide, but is more commonly called thioanisole, since its structure is related to that for anisole, C6H5OCH3. The modern sy ...
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Transition Metal Thioether Complex
Transition metal thioether complexes comprise coordination complexes of thioether (R2S) ligands. The inventory is extensive. Dimethylsulfide complexes As the simplest thioether, dimethyl sulfide forms complexes that are illustrative of the class. Well characterized derivatives include ''cis''- iCl4L2 VCl3L2, NbCl5L, NbCl4L2, Cr(CO)5L, CrCl3L3, RuCl2L4, RuCl3L3, RhCl3L3, ''cis''- and ''trans''- rCl4L3, ''cis''-MCl2L2 (M = Pd, Pt), tCl3Lsup>−, ''cis''- and ''trans''- tCl4L2(L = SMe2). With respect to donor properties, dimethyl sulfide is a soft ligand with donor properties weaker than phosphine ligands. Such complexes are generally prepared by treating the metal halide with the thioether. Chloro(dimethyl sulfide)gold(I) can however be prepared by redox reaction of elemental gold and DMSO in the presence of hydrochloric acid. Stereochemistry Thioether complexes feature pyramidal sulfur centers. Typical C-S-C angles are near 99° in both free thioethers and their complexe ...
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Alkylation
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents. Nucleophilic alkylating agents Nucleophilic alkylating agents deliver the equivalent of an alkyl anion ( carbanion). The formal "alkyl anion" attacks an electrophile, forming a new covalent ...
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Thioethers
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 sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application. Nomenclature Sulfides are sometimes called thioethers, especially in the old literature. The two organic substituents are indicated by the prefixes. (CH3)2S is called dimethylsulfide. Some sulfides are named by modifying the common name for the corresponding ether. For example, C6H5SCH3 is methyl phenyl sulfide, but is more commonly called thioanisole, since its structure is related to that for anisole, C6H5OCH3. The modern s ...
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Chelating Agents
Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are called chelants, chelators, chelating agents, or sequestering agents. They are usually organic compounds, but this is not a necessity, as in the case of zinc and its use as a maintenance therapy to prevent the absorption of copper in people with Wilson's disease. Chelation is useful in applications such as providing nutritional supplements, in chelation therapy to remove toxic metals from the body, as contrast agents in MRI scanning, in manufacturing using homogeneous catalysts, in chemical water treatment to assist in the removal of metals, and in fertilizers. Chelate effect The chelate effect is the greater affinity of chelating ligands for a metal ion than that of similar nonchelating (monodentate) ligands for the same metal. ...
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Sulfur Heterocycles
Sulfur (or sulphur in British English) is a chemical element with the Symbol (chemistry), symbol S and atomic number 16. It is abundance of the chemical elements, abundant, Polyvalency (chemistry), multivalent and nonmetallic. Under standard conditions for temperature and pressure, normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula octasulfur, S8. Elemental sulfur is a bright yellow, crystalline solid at room temperature. Sulfur is the tenth most abundant element by mass in the universe and the fifth most on Earth. Though sometimes found in pure, native element minerals, native form, sulfur on Earth usually occurs as sulfide minerals, sulfide and sulfate minerals. Being abundant in native form, sulfur was known in ancient times, being mentioned for its uses in ancient India, ancient Greece, history of China#Ancient China, China, and ancient Egypt. Historically and in literature sulfur is also called brimstone, which means "burning stone". To ...
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