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Sulfinamide
Sulfinamide is a functional group in organosulfur chemistry with the structural formula RS(O)NR'2 (where R and R' are organic substituents). This functionality is composed of a sulfur-carbon (S–C) and sulfur-nitrogen (S–N) single bonds, as well as a sulfur-oxygen double bond (S=O), resulting in a tetravalent sulfur centre (in resonance with its zwitterionic form). As a non-bonding electron pair is also present on the sulfur, these compounds are also chiral. They are sometimes referred to as ''S''-chiral sulfinamides. Sulfinamides are amides of sulfinic acid (RS(O)OH). Structure Sulfinamides do not undergo inversion. They can therefore be synthesised and/or isolated in enantiopure forms. This has led to their use as chiral ammonia equivalents and more broadly as chiral auxiliaries. Synthesis Sulfinamides are traditionally produced by the reaction of sulfinyl chlorides with primary or secondary amines. They also arise by the addition of Grignard reagents to sulfinylamines ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tert-Butanesulfinamide
''tert''-Butanesulfinamide (also known as 2-methyl-2-propanesulfinamide or Ellman's sulfinamide) is an organosulfur compound and a member of the class of sulfinamides. Both enantiomeric forms are commercially available and are used in asymmetric synthesis as chiral auxiliaries, often as chiral ammonia equivalents for the synthesis of amines. ''tert''-Butanesulfinamide and the associated synthetic methodology was introduced in 1997 by Jonathan A. Ellman ''et al''. Enantiopure synthesis Enantiopure ''tert''-butanesulfinamide can be prepared by enantioselective oxidation of inexpensive di-''tert''-butyl disulfide to the thiosulfinate followed by disulfide bond cleavage by lithium amide. In the original scope the chiral ligand used together with vanadyl acetylacetonate was prepared by condensing an optically pure chiral aminoindanol with 3,5-di-''tert''-butyl salicylaldehyde. Enantioselective amine synthesis Condensation with ketones and aldehydes yields the corresponding ' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chiral Auxiliary
In stereochemistry, a chiral auxiliary is a stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis. The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions. The auxiliary can then be typically recovered for future use. Most biological molecules and pharmaceutical targets exist as one of two possible enantiomers; consequently, chemical syntheses of natural products and pharmaceutical agents are frequently designed to obtain the target in enantiomerically pure form. Chiral auxiliaries are one of many strategies available to synthetic chemists to selectively produce the desired stereoisomer of a given compound. Chiral auxiliaries were introduced by Elias James Corey in 1975 with chiral 8-phenylmenthol and by Barry Trost in 1980 with chiral mandelic acid. The menthol compound is difficult to prepare and as an alternative trans-2-phenyl-1-c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfinamide Structure
Sulfinamide is a functional group in organosulfur chemistry with the structural formula RS(O)NR'2 (where R and R' are organic substituents). This functionality is composed of a sulfur-carbon (S–C) and sulfur-nitrogen (S–N) single bonds, as well as a sulfur-oxygen double bond (S=O), resulting in a tetravalent sulfur centre (in resonance with its zwitterionic form). As a non-bonding electron pair is also present on the sulfur, these compounds are also chiral. They are sometimes referred to as ''S''-chiral sulfinamides. Sulfinamides are amides of sulfinic acid (RS(O)OH). Structure Sulfinamides do not undergo inversion. They can therefore be synthesised and/or isolated in enantiopure forms. This has led to their use as chiral ammonia equivalents and more broadly as chiral auxiliaries. Synthesis Sulfinamides are traditionally produced by the reaction of sulfinyl chlorides with primary or secondary amines. They also arise by the addition of Grignard reagents to sulfinylamines, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organosulfur Chemistry
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 compound ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfinyl Chloride
Sulfinyl halide have the general formula R−S(O)−X, where X is a halogen. They are intermediate in oxidation level between sulfenyl halides, R−S−X, and sulfonyl halides, R−SO2−X. The best known examples are sulfinyl chlorides, thermolabile, moisture-sensitive compounds, which are useful intermediates for preparation of other sufinyl derivatives such as sulfinamides, sulfinates, sulfoxides, and thiosulfinates. Unlike the sulfur atom in sulfonyl halides and sulfenyl halides, the sulfur atom in sulfinyl halides is chiral, as shown for methanesulfinyl chloride. Sulfinyl chlorides Sulfinic acid chlorides, or sulfinyl chlorides, are sulfinyl halides with the general formula R−S(O)−Cl. Methanesulfinyl chloride, CH3S(O)Cl, is prepared by chlorination of dimethyl disulfide to give CH3SCl3, which is treated with acetic anhydride. It is a straw-colored liquid. Toluenesulfinyl chloride is prepared by treating sodium tosylate with thionyl chloride: Also a straw-colored liqu ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nitroxyl
Nitroxyl (common name) or azanone (IUPAC name) is the chemical compound HNO. It is well known in the gas phase. Nitroxyl can be formed as a short-lived intermediate in the solution phase. The conjugate base, NO−, nitroxide anion, is the redox reaction, reduced form of nitric oxide (NO) and is isoelectronic with dioxygen. The bond dissociation energy of H−NO is , which is unusually weak for a bond to the hydrogen atom. Generation Nitroxyl is produced from the reagents Angeli's salt (Na2N2O3) and Piloty's acid (PhSO2NHOH). Other notable studies on the production of HNO exploit cycloadducts of acyl nitroso species, which are known to decompose via hydrolysis to HNO and acyl acid. Upon photodissociation, photolysis these compounds release the acyl nitroso species which then further decompose. HNO is generated via organic oxidation of oxime, cyclohexanone oxime with lead tetraacetate to form 1-nitrosocyclohexyl acetate: : This compound can be hydrolyzed under base (chemistry), bas ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Amides
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid () with the hydroxyl group () replaced by an amine group (); or, equivalently, an acyl (alkanoyl) group () joined to an amine group. Common examples of amides are acetamide (), benzamide (), and dimethylformamide (). Amides are qualified as primary, secondary, and tertiary according to whether the amine subgroup has the form , , or , where R and R' are groups other than hydrogen. The core of amides is called the amide group (specifically, carboxamide group). Amides are pervasive in nature and technology. Proteins and important plastics ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thiol
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols (that is, sulfur takes the place of oxygen in the hydroxyl () group of an alcohol), and the word is a blend of "''thio-''" with "alcohol". Many thiols have strong odors resembling that of garlic or rotten eggs. Thiols are used as odorants to assist in the detection of natural gas (which in pure form is odorless), and the "smell of natural gas" is due to the smell of the thiol used as the odorant. Thiols are sometimes referred to as mercaptans () or mercapto compounds, a term introduced in 1832 by William Christopher Zeise and is derived from the Latin ('capturing mercury')''Oxford American Dictionaries'' (Mac OS X Leopard). because the thiolate group () bonds very strong ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Franklin A
Franklin may refer to: People * Franklin (given name) * Franklin (surname) * Franklin (class), a member of a historical English social class Places Australia * Franklin, Tasmania, a township * Division of Franklin, federal electoral division in Tasmania * Division of Franklin (state), state electoral division in Tasmania * Franklin, Australian Capital Territory, a suburb in the Canberra district of Gungahlin * Franklin River, river of Tasmania * Franklin Sound, waterway of Tasmania Canada * District of Franklin, a former district of the Northwest Territories * Franklin, Quebec, a municipality in the Montérégie region * Rural Municipality of Franklin, Manitoba * Franklin, Manitoba, an unincorporated community in the Rural Municipality of Rosedale, Manitoba * Franklin Glacier Complex, a volcano in southwestern British Columbia * Franklin Range, a mountain range on Vancouver Island, British Columbia * Franklin River (Vancouver Island), British Columbia * Franklin Strait, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mesityl
Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds. Preparation Mesitylene is prepared by transalkylation of xylene over solid acid catalyst:Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke “Hydrocarbons” in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. . :2 C6H4(CH3)2 ⇌ C6H3(CH ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfinylamine
153 px, ''N''-Sulfinylaniline is a common sulfinylamine. Sulfinylamines (formerly ''N''-sulfinyl amines) are organosulfur compounds with the formula RNSO where R = an organic substituent. These compounds are, formally speaking, derivatives of HN=S=O, i.e. analogues of sulfur dioxide and of sulfur diimide. A common example is ''N''-sulfinylaniline. Sulfinyl amines are dienophile.Kresze, G.; Wucherpfennig, W., "Organic synthesis with imides of sulfur dioxide", Angew. Chem. Int. Ed. Engl. 1967, volume 6, 149–167. They undergo +2cycloaddition to ketenes. According to X-ray crystallography, sulfinylamines have planar C-N=S=O cores with ''syn'' geometry.. Preparation Sulfinylamines can be made when thionyl chloride SOCl2 reacts with a primary amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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