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Sodium Methylsulfinylmethylide
Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of the conjugate base of dimethyl sulfoxide. This unusual salt has some uses in organic chemistry as a base and nucleophile. Since the first publication in 1965 by Corey ''et al.'', a number of additional uses for this reagent have been identified. Preparation Sodium methylsulfinylmethylide is prepared by heating sodium hydride or sodium amide in DMSO :CH3SOCH3 + NaH → CH3SOCH2−Na+ + H2 :CH3SOCH3 + NaNH2 → CH3SOCH2−Na+ + NH3 Reactions As a Base The pKa of DMSO is 35, which leads NaDMSO to be a powerful Brønsted base. NaDMSO is used in the generation of phosphorus and sulfur ylides. NaDMSO in DMSO is especially convenient in the generation of dimethyloxosulfonium methylide and dimethylsulfonium methylide. Reaction with esters NaDMSO condenses with esters (1) to form β-ketosulfoxides (2), which can be useful intermediates. Reduction of β-ketosulfoxides with aluminium ama ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dimethyl Sulfoxide
Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO has the unusual property that many individuals perceive a garlic-like taste in the mouth after DMSO makes contact with their skin. In terms of chemical structure, the molecule has idealized Cs symmetry. It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds, with a nonbonded electron pair on the approximately tetrahedral sulfur atom. Synthesis and production Dimethyl sulfoxide was first synthesized in 1866 by the Russian scientist Alexander Zaytsev, who reported his findings in 1867. Dimethyl sulfoxide is produced industrially from dimethyl sulfide, a by-product of the Kraf ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Barry M
Barry M is a British cruelty-free cosmetics company, specializing in on trend make-up and nail products. Based in Mill Hill East, London London is the capital and largest city of England and the United Kingdom, with a population of just under 9 million. It stands on the River Thames in south-east England at the head of a estuary down to the North Sea, and has been a majo ..., it was founded by Barry Mero in 1982. Employing over 80 people in a 45,000 square foot production, distribution and warehouse facility in Mill Hill, the company generates an estimated $17m in annual sales supplying retailers such as Boots, ASOS, PYT, Superdrug and Tesco. Barry Mero started his business life as a boy selling nail polishes on a stall in his mother's front garden. Years later he moved into retail with a shop in Ridley Road Market, London. Specializing in bold, vibrant make up colours, in 1982 he created his own brand – Barry M(ero). Moving to North London, to Mill Hill East, Ba ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Gaylord Chemical Corporation
The company headquarters of Gaylord Chemical Company LLC are located in the New Orleans suburb of Slidell, Louisiana, USA. Gaylord's original manufacturing facility located in Bogalusa, Louisiana was shut down and demolished in 2010, when the company relocated its operations to Tuscaloosa, Alabama, USA. The company has manufactured dimethyl sulfoxide (DMSO) and dimethyl sulfide (DMS) continuously since the early 1960s. Prior to its acquisition by its management team in 2007 Gaylord operated as a wholly owned subsidiary of Temple-Inland Inc. (NYSE: TIN). After the ownership transition was complete it continued to operate from its Slidell office, which had been established in the late 1980s. Gaylord announced expanded DMSO production capacity in Tuscaloosa, Alabama, which came on-line in 2010. Prior to being a subsidiary of Temple-Inland, Gaylord Chemical was a division of Gaylord Container Corporation, the successor (1986–2002) of the brown paper division of Crown Zellerbach (192 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
NaDMSO Nucleophilic Reactions
Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of the conjugate base of dimethyl sulfoxide. This unusual salt has some uses in organic chemistry as a base and nucleophile. Since the first publication in 1965 by Corey ''et al.'', a number of additional uses for this reagent have been identified. Preparation Sodium methylsulfinylmethylide is prepared by heating sodium hydride or sodium amide in DMSO :CH3SOCH3 + NaH → CH3SOCH2−Na+ + H2 :CH3SOCH3 + NaNH2 → CH3SOCH2−Na+ + NH3 Reactions As a Base The pKa of DMSO is 35, which leads NaDMSO to be a powerful Brønsted base. NaDMSO is used in the generation of phosphorus and sulfur ylides. NaDMSO in DMSO is especially convenient in the generation of dimethyloxosulfonium methylide and dimethylsulfonium methylide. Reaction with esters NaDMSO condenses with esters (1) to form β-ketosulfoxides (2), which can be useful intermediates. Reduction of β-ketosulfoxides with aluminium ama ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Synthesis (journal)
''Synthesis'' is a scientific journal published from 1969 to the present day by Thieme Medical Publishers, Thieme. Its stated purpose is the "advancement of the science of synthetic chemistry". From August 2006, selected articles are offered free of charge. The impact factor of this journal is 2.867 (2018).Journal Citation Reports, 2018 References [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 carbonyl group is often referred to as a carbonyl compound. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g. nickel carbonyl). The remainder of this article concerns itself with the organic chemistry definition of carbonyl, where carbon and oxygen share a double bond. Carbonyl compounds In organic chemistry, a carbonyl group characterizes the following types of compounds: Other organic carbonyls are urea and the carbamates, the derivatives of acyl chlorides chloroformates and phosgene, carbonate esters, thioesters, lactones, lactams, hydroxamates, and isocyanates. Examples of inorganic carbonyl compounds are carbon dioxide and carbonyl sulfide. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pummerer Rearrangement
The Pummerer rearrangement is an organic reaction whereby an alkyl sulfoxide rearranges to an α- acyloxy–thioether (monothioacetal-ester) in the presence of acetic anhydride. The stoichiometry of the reaction is: :RS(O)CHR'2 + Ac2O → RSC(OAc)R'2 + AcOH Synthetic implementation Aside from acetic anhydride, trifluoroacetic anhydride and trifluoromethanesulfonic anhydride have been employed as activators. Common nucleophiles besides acetates are arenes, alkenes, amides, and phenols. The usage of α-acyl sulfoxides and Lewis acids, such as TiCl4 and SnCl4, allow the reaction to proceed at lower temperatures (0 °C). Thionyl chloride can be used in place of acetic anhydride to trigger the elimination for forming the electrophilic intermediate and supplying chloride as the nucleophile to give an α-chloro-thioether: Other anhydrides and acyl halides can give similar products. Inorganic acids can also give this reaction. This product can be converted to aldehyd ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Elimination Reaction
An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists. Finally, the pyrolysis of xanthate and acetate esters proceed through an "internal" elimination mechanism, the Ei mechanism. E2 mechanism The E2 mechanism, where E2 stands for bimolecular elimination, involves a one-step mechanism in which ''carbon-hydrogen'' and ''carbon-halogen'' bonds break to form a double bond (''C=C Pi bond''). The specifics of the reaction are as follows: * E2 is a single step elimination, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considere ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methyl
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond (), it can be found on its own in any of three forms: methanide anion (), methylium cation () or methyl radical (). The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed. Methyl cation, anion, and radical Methyl cation The methylium cation () exists in the gas phase, but is otherwise not encountered. Some compounds are considered to be sources of the cation, and this simplification is used pervasively in organic chemistry. For example, protonation of methanol gives an elect ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aluminium Amalgam
Aluminium can form an amalgam in solution with mercury. Aluminium amalgam may be prepared by either grinding aluminium pellets or wire in mercury, or by allowing aluminium wire to react with a solution of mercury(II) chloride in water. This amalgam is used as a chemical reagent to reduce compounds, such as the reduction of imines to amines. The aluminium is the ultimate electron donor, and the mercury serves to mediate the electron transfer. The reaction and the waste from it contains mercury, so special safety precautions and disposal methods are needed. As an environmentally friendlier alternative, hydrides or other reducing agents can often be used to accomplish the same synthetic result. An alloy of aluminium and gallium was proposed as a method of hydrogen generation, as the gallium renders the aluminium more reactive by preventing it from forming an oxide layer. Mercury has this same effect on aluminium, but also serves additional functions related to electron transfer tha ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties. '' Nomenclature Etymology Th ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
