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The Appel reaction is an organic reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride. The use of carbon tetrabromide or bromine as a halide source will yield alkyl bromides, whereas using carbon tetraiodide, methyl iodide or iodine gives alkyl iodides. The reaction is credited to and named after Rolf Appel, it had however been described earlier. The use of this reaction is becoming less common, due to carbon tetrachloride being restricted under the Montreal protocol.
Lawesson's reagent (LR) is a chemical compound used in organic synthesis as a thiation agent. Lawesson's reagent was first made popular by Sven-Olov Lawesson, who did not, however, invent it. Lawesson's reagent was first made in 1956 during a systematic study of the reactions of arenes with P4S10.
The Reformatsky reaction is an organic reaction which condenses aldehydes or ketones with α-halo esters using metallic zinc to form β-hydroxy-esters:
Organoselenium chemistry is the science exploring the properties and reactivity of organoselenium compounds, chemical compounds containing carbon-to-selenium chemical bonds. Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected. Organoselenium compounds are found at trace levels in ambient waters, soils and sediments.
The Sakurai reaction is the chemical reaction of carbon electrophiles with allyltrimethylsilane catalyzed by strong Lewis acids.
Tebbe's reagent is the organometallic compound with the formula (C5H5)2TiCH2ClAl(CH3)2. It is used in the methylidenation of carbonyl compounds, that is it converts organic compounds containing the R2C=O group into the related R2C=CH2 derivative. It is a red solid that is pyrophoric in the air, and thus is typically handled with air-free techniques. It was originally synthesized by Fred Tebbe at DuPont Central Research.
The Petasis reagent, named after Nicos A. Petasis, is an organotitanium compound with the formula Cp2Ti(CH3)2. It is an orange-colored solid.
Organozinc chemistry is the study of the physical properties, synthesis, and reactions of organozinc compounds, which are organometallic compounds that contain carbon (C) to zinc (Zn) chemical bonds.
Dicobalt octacarbonyl is an organocobalt compound with composition Co2(CO)8. This metal carbonyl is used as a reagent and catalyst in organometallic chemistry and organic synthesis, and is central to much known organocobalt chemistry. It is the parent member of a family of hydroformylation catalysts. Each molecule consists of two cobalt atoms bound to eight carbon monoxide ligands, although multiple structural isomers are known. Some of the carbonyl ligands are labile.
The Wurtz–Fittig reaction is the chemical reaction of aryl halides with alkyl halides and sodium metal in the presence of dry ether to give substituted aromatic compounds. Charles Adolphe Wurtz reported what is now known as the Wurtz reaction in 1855, involving the formation of a new carbon-carbon bond by coupling two alkyl halides. Work by Wilhelm Rudolph Fittig in the 1860s extended the approach to the coupling of an alkyl halide with an aryl halide. This modification of the Wurtz reaction is considered a separate process and is named for both scientists.
Diphenyl diselenide is the chemical compound with the formula (C6H5)2Se2, abbreviated Ph2Se2. This orange-coloured solid is the oxidized derivative of benzeneselenol. It is used as a source of the PhSe unit in organic synthesis.
Organotitanium chemistry is the science of organotitanium compounds describing their physical properties, synthesis, and reactions. Organotitanium compounds in organometallic chemistry contain carbon-titanium chemical bonds. They are reagents in organic chemistry and are involved in major industrial processes.
The Kulinkovich reaction describes the organic synthesis of substituted cyclopropanols through reaction of esters with dialkyldialkoxytitanium reagents, which are generated in situ from Grignard reagents containing a hydrogen in beta-position and titanium(IV) alkoxides such as titanium isopropoxide. This reaction was first reported by Oleg Kulinkovich and coworkers in 1989.
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Electrophilic amination is a chemical process involving the formation of a carbon–nitrogen bond through the reaction of a nucleophilic carbanion with an electrophilic source of nitrogen.
Reductions with samarium(II) iodide involve the conversion of various classes of organic compounds into reduced products through the action of samarium(II) iodide, a mild one-electron reducing agent.
Desulfonylation reactions are chemical reactions leading to the removal of a sulfonyl group from organic compounds. As the sulfonyl functional group is electron-withdrawing, methods for cleaving the sulfur–carbon bonds of sulfones are typically reductive in nature. Olefination or replacement with hydrogen may be accomplished using reductive desulfonylation methods.
Trifluoromethylation in organic chemistry describes any organic reaction that introduces a trifluoromethyl group in an organic compound. Trifluoromethylated compounds are of some importance in pharmaceutical industry and agrochemicals. Several notable pharmaceutical compounds have a trifluoromethyl group incorporated: fluoxetine, mefloquine, Leflunomide, nulitamide, dutasteride, bicalutamide, aprepitant, celecoxib, fipronil, fluazinam, penthiopyrad, picoxystrobin, fluridone, norflurazon, sorafenib and triflurazin. A relevant agrochemical is trifluralin. The development of synthetic methods for adding trifluoromethyl groups to chemical compounds is actively pursued in academic research.
In organic chemistry, the Davis oxidation or Davis' oxaziridine oxidation refers to oxidations involving the use of the Davis reagent or other similar oxaziridine reagents. This reaction mainly refers to the generation of α-hydroxy carbonyl compounds (acyloins) from ketones or esters. The reaction is carried out in a basic environment to generate the corresponding enolate from the ketone or ester. This reaction has been shown to work for amides.
In organic chemistry, methylenation is a chemical reaction that inserts a methylene group into a chemical compound:
References
- ↑ Lombardo, Luciano (1982-07-27). "Methylenation of carbonyl compounds with ZnCH2Br2TiCl4. Application to gibberellins". Tetrahedron Letters. 23 (41): 4293–4296. doi:10.1016/S0040-4039(00)88728-6.
- ↑ Wang, Zerong (15 September 2010). Comprehensive Organic Name Reactions and Reagents. doi:10.1002/9780470638859.conrr397. ISBN 9780470638859.
- ↑ Kulinkovich, Oleg G.; Meijere, Armin de (2000-07-21). "1,n-Dicarbanionic Titanium Intermediates from Monocarbanionic Organometallics and Their Application in Organic Synthesis". Chemical Reviews. 100 (8): 2789–2834. doi:10.1021/cr980046z. PMID 11749306.
- ↑ Pine, Stanley H. (2004-08-15). "Carbonyl Methylenation and Alkylidenation Using Titanium-Based Reagents". Organic Reactions: 1–91. doi:10.1002/0471264180.or043.01. ISBN 0471264180.
- ↑ Hartley, Richard C.; Li, Jianfeng; Main, Calver A.; McKiernan, Gordon J. (2007-06-04). "Titanium carbenoid reagents for converting carbonyl groups into alkenes". Tetrahedron. 63 (23): 4825–4864. doi:10.1016/j.tet.2007.03.015.
- ↑ Luciano Lombardo (1987). "Methylenation of Carbonyl Compounds: (+)-3-Methylene-cis-p-menthane". Organic Syntheses. 65: 81. doi:10.15227/orgsyn.065.0081.
- ↑ Marsden, Stephen P.; Ducept, Pascal C. (2005). "Synthesis of highly substituted allenylsilanes by alkylidenation of silylketenes". Beilstein Journal of Organic Chemistry . 1 (1): 5. doi: 10.1186/1860-5397-1-5 . PMC 1399453 . PMID 16542018.
- ↑ Hinman, Andrew; Du Bois, Justin (2003-08-30). "A Stereoselective Synthesis of (−)-Tetrodotoxin". Journal of the American Chemical Society. 125 (38): 11510–11511. doi:10.1021/ja0368305. PMID 13129349.
- ↑ Ley, Steven V.; Murray, P. John (1982). "A short syntesis of (±)-hirsutene involving the use of an organoselenium-mediated cyclization reaction". Journal of the Chemical Society, Chemical Communications (21): 1252–1253. doi:10.1039/C39820001252.
- ↑ Ley, Steven V.; Murray, P. John; Palmer, Brian D. (1985-11-14). "Total synthesis of the sesquiterpene (±)-hirsutene using an organoselenium-mediated cyclization reaction". Tetrahedron. 41 (21): 4765–4769. doi:10.1016/S0040-4020(01)96715-8.
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