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Tosyl
In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or TosIn this article, "Ts", unless otherwise stated, means tosyl, not tennessine.) is a univalent functional group with the chemical formula . It consists of a tolyl group, , joined to a sulfonyl group, , with the open valence on sulfur. This group is usually derived from the compound tosyl chloride, (abbreviated TsCl), which forms esters and amides of toluenesulfonic acid, (abbreviated TsOH). The para orientation illustrated (''p''-toluenesulfonyl) is most common, and by convention ''tosyl'' without a prefix refers to the ''p''-toluenesulfonyl group. The tosyl terminology was proposed by German chemists Kurt Hess and Robert Pfleger in 1933 on the pattern of trityl and adopted in English starting from 1934. The toluenesulfonate (or tosylate) group refers to the (–OTs) group, with an additional oxygen attached to sulfur and open valence on an oxygen. In a chemical name, the term ''tosylate'' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
4-Toluenesulfonyl Chloride
4-Toluenesulfonyl chloride (''p''-toluenesulfonyl chloride, toluene-''p''-sulfonyl chloride) is an organic compound with the formula CH3C6H4SO2Cl. This white, malodorous solid is a reagent widely used in organic synthesis. Abbreviated TsCl or TosCl, it is a derivative of toluene and contains a sulfonyl chloride (−SO2Cl) functional group. Uses As typical for Sulfonyl halides, TsCl converts alcohols (abbreviated ROH) into the corresponding toluenesulfonate esters, or tosyl derivatives ("tosylates"): : CH3C6H4SO2Cl + ROH → CH3C6H4SO2OR + HCl Tosylates can be cleaved with lithium aluminium hydride: : 4 CH3C6H4SO2OR + LiAlH4 → LiAl(O3SC6H4CH3)4 + 4 RH Thus, tosylation followed by reduction allows for removal of a hydroxyl group. Likewise, TsCl is used to prepare sulfonamides from amines: :CH3C6H4SO2Cl + R2NH → CH3C6H4SO2NR2 + HCl The resulting sulfonamides are non-basic and, when derived from primary amines, are even acidic. TsCl reacts with hydrazine ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfonyl
In organosulfur chemistry, a sulfonyl group is either a functional group found primarily in sulfones, or a substituent obtained from a sulfonic acid by the removal of the hydroxyl group, similarly to acyl groups. Group Sulfonyl groups can be written as having the general formula , where there are two double bonds between the sulfur and oxygen. Sulfonyl groups can be reduced to the sulfide with diisobutylaluminium hydride (DIBALH). Lithium aluminium hydride () reduces some but not all sulfones to sulfides. In inorganic chemistry, when the group is not connected to any carbon atoms, it is referred to as sulfuryl. Examples of sulfonyl group substituents The names of sulfonyl groups typically end in -syl, such as: : See also * Sulfonyl halide * Sulfonamide * Sulfonate * Methylsulfonylmethane Dimethyl sulfone (DMSO2) is an organosulfur compound with the formula . It is also known by several other names including methyl sulfone and (especially in alternative medicine) methyl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 preparations of delicate organic compounds, specific parts of the molecules cannot survive the required reagents or chemical environments. These parts (functional groups) must be protected. For example, lithium aluminium hydride is a highly reactive reagent that usefully reduces esters to alcohols. It always reacts with carbonyl groups, and cannot be discouraged by any means. When an ester must be reduced in the presence of a carbonyl, hydride attack on the carbonyl must be prevented. One way to do so converts the carbonyl into an acetal, which does not react with hydrides. The acetal is then called a protecting group for the carbonyl. After the hydride step is complete, aqueous acid removes the acetal, restoring the carbonyl. This step ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
SN2 Reaction
The bimolecular nucleophilic substitution (SN2) is a type of reaction mechanism that is common in organic chemistry. In the SN2 reaction, a strong nucleophile forms a new bond to an sp3-hybridised carbon atom via a backside attack, all while the leaving group detaches from the reaction center in a concerted (i.e. simultaneous) fashion. The name SN2 refers to the Hughes-Ingold symbol of the mechanism: "SN" indicates that the reaction is a nucleophilic substitution, and "2" that it proceeds via a bimolecular mechanism, which means both the reacting species are involved in the rate-determining step. What distinguishes SN2 from the other major type of nucleophilic substitution, the SN1 reaction, is that the displacement of the leaving group, which is the rate-determining step, is separate from the nucleophilic attack in SN1. The SN2 reaction can be considered as an organic-chemistry analogue of the associative substitution from the field of inorganic chemistry. Reaction mech ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Iron(III) Chloride
Iron(III) chloride describes the inorganic compounds with the formula (H2O)x. Also called ferric chloride, these compounds are some of the most important and commonplace compounds of iron. They are available both in anhydrous and in hydrated forms, which are both hygroscopic. They feature iron in its +3 oxidation state. The anhydrous derivative is a Lewis acid, while all forms are mild oxidizing agents. It is used as a water cleaner and as an etchant for metals. Electronic and optical properties All forms of ferric chloride are paramagnetic, owing to the presence of unpaired electrons residing in 3d orbitals. Although Fe(III) chloride can be octahedral or tetrahedral (or both, see structure section), all of these forms have five unpaired electrons, one per d-orbital. The high spin d5 electronic configuration requires that d-d electronic transitions are spin forbidden, in addition to violating the Laporte rule. This double forbidden-ness results in its solutions being ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
P-cresol
''para''-Cresol, also 4-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of ''o''-cresol and ''m''-cresol. Production Together with many other compounds, ''p''-cresol is conventionally extracted from coal tar, the volatilized materials obtained in the roasting of coal to produce coke. This residue contains a few percent by weight of phenol and cresols. Industrially, ''p''-cresol is currently prepared mainly by a two-step route beginning with the sulfonation of toluene: :CH3C6H5 + H2SO4 → CH3C6H4SO3H + H2O Basic hydrolysis of the sulfonate salt gives the sodium salt of the cresol: :CH3C6H4SO3H + 2 NaOH → CH3C6H4OH + Na2SO3 + H2O Other methods for the production of ''p''-cresol include chlorination of toluene followed by hydrolysis. In the cymene-cresol process, toluene is alkylated with propene to give ''p''-cy ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sodium Hydroxide
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), base and alkali that decomposes lipids and proteins at ambient temperatures and at high concentrations may cause severe chemical burns. It is highly soluble in water, and readily absorbs moisture and carbon dioxide from the air. It forms a series of hydrates . The monohydrate crystallizes from water solutions between 12.3 and 61.8 °C. The commercially available "sodium hydroxide" is often this monohydrate, and published data may refer to it instead of the anhydrous compound. As one of the simplest hydroxides, sodium hydroxide is frequently used alongside neutral water and acidic hydrochloric acid to demonstrate the pH scale to chemistry students. Sodium hydroxide is used in many industries: in the making of wood pulp and paper, tex ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sodium Borohydride
Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula (sometimes written as ). It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodium borohydride is a reducing agent that finds application in papermaking and dye industries. It is also used as a reagent in organic synthesis. The compound was discovered in the 1940s by H. I. Schlesinger, who led a team seeking volatile uranium compounds.Hermann I Schlesinger and Herbert C Brown (1945)Preparation of alkali metal compounds. US Patent 2461661. Granted on 1949-02-15; expired on 1966-02-15. Results of this wartime research were declassified and published in 1953. Properties The compound is soluble in alcohols, certain ethers, and water, although it slowly hydrolyzes. Sodium borohydride is an odorless white to gray-white microcrystalline powder that often forms lumps. It can be purified by recrystallization from warm ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Reduction
Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions, because many reactions carry the name but do not actually involve electron transfer.March Jerry; (1985). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc. Instead the relevant criterion for organic oxidation is gain of oxygen and/or loss of hydrogen.''Organic Redox Systems: Synthesis, Properties, and Applications'', Tohru Nishinaga 2016 Simple functional groups can be arranged in order of increasing oxidation state. The oxidation numbers are only an approximation: When methane is oxidized to carbon dioxide its oxidation number changes from −4 to +4. Classical reductions include alkene reduction to alkanes and classical oxidations include oxidation of alcohols to aldehydes. In oxidations electrons ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Process Research & Development
''Organic Process Research & Development'' is a peer-reviewed scientific journal published since 1997 by the American Chemical Society. Its publication frequency switched from bimonthly to monthly in 2012. It is indexed in Chemical Abstracts Service, Scopus, EBSCOhost, British Library, and Web of Science. The current editor-in-chief is Kai Rossen. According to the ''Journal Citation Reports'', the journal has a 2021 impact factor The impact factor (IF) or journal impact factor (JIF) of an academic journal is a type of journal ranking. Journals with higher impact factor values are considered more prestigious or important within their field. The Impact Factor of a journa ... of 3.858. References External links * {{DEFAULTSORT:Organic Process Research and Development American Chemical Society academic journals Monthly journals Academic journals established in 1997 English-language journals Pharmaceutical sciences ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diisopropylamine
Diisopropylamine is a secondary amine with the chemical formula (Me2CH)2NH (Me = methyl). Diisopropylamine is a colorless liquid with an ammonia-like odor. Its lithium derivative, lithium diisopropylamide, known as LDA is a widely used reagent. Reactions and use Diisopropylamine is a common amine nucleophile in organic synthesis. Because it is bulky, it is a more selective nucleophile than other similar amines, such as dimethylamine. It reacts with organolithium reagents to give lithium diisopropylamide (LDA). LDA is a strong, non-nucleophilic base The main commercial applications of diisopropylamine is as a precursor to the herbicide, diallate and triallate as well as certain sulfenamides used in the vulcanization of rubber. It is also used to prepare ''N'',''N''-diisopropylethylamine (Hünig's base) by alkylation with diethyl sulfate. The bromide salt of diisopropylamine, diisopropylammonium bromide, is a room-temperature organic ferroelectric material. Preparation D ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
