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Oxaphosphetane
An oxaphosphetane is a molecule containing a four-membered ring with one phosphorus, one oxygen and two carbon atoms. In a 1,2-oxaphosphetane phosphorus is bonded directly to oxygen, whereas a 1,3-oxaphosphetane has the phosphorus and oxygen atoms at opposite corners. 1,2-Oxaphosphetanes are rarely isolated but are important intermediates in the Wittig reaction and related reactions such as the Seyferth–Gilbert homologation and the Horner–Wadsworth–Emmons reaction. Edwin Vedejs's NMR Nuclear magnetic resonance (NMR) is a physical phenomenon in which nuclei in a strong constant magnetic field are perturbed by a weak oscillating magnetic field (in the near field) and respond by producing an electromagnetic signal with a ... studies first revealed the importance of oxaphosphetanes in the mechanism of the Wittig reaction in the 1970s. References Phosphorus heterocycles Oxygen heterocycles Four-membered rings {{heterocyclic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Wittig Reaction
The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes. Most often, the Wittig reaction is used to introduce a methylene group using methylenetriphenylphosphorane (Ph3P=CH2). Using this reagent, even a sterically hindered ketone such as camphor can be converted to its methylene derivative. Stereochemistry For the reaction with aldehydes, the double bond geometry is readily predicted based on the nature of the ylide. With unstabilised ylides (R3 = alkyl) this results in (''Z'')-alkene product with moderate to high selectivity. With stabilized ylides (R3 = ester or ketone), the (''E'')-alkene is formed with high selectivity. The (''E'')/(''Z'') selectivity is often poor with semistabilized ylides (R3 = aryl). To obtain the (''E'')-alkene for unstabilized ylides, the Schlosser modification of the W ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Horner–Wadsworth–Emmons Reaction
The Horner–Wadsworth–Emmons (HWE) reaction is a chemical reaction used in organic chemistry of stabilized phosphonate carbanions with aldehydes (or ketones) to produce predominantly E-alkenes. In 1958, Leopold Horner published a modified Wittig reaction using phosphonate-stabilized carbanions. William S. Wadsworth and William D. Emmons further defined the reaction. In contrast to phosphonium ylides used in the Wittig reaction, phosphonate-stabilized carbanions are more nucleophilic but less basic. Likewise, phosphonate-stabilized carbanions can be alkylated. Unlike phosphonium ylides, the dialkylphosphate salt byproduct is easily removed by aqueous extraction. Several reviews have been published. Reaction mechanism The Horner–Wadsworth–Emmons reaction begins with the deprotonation of the phosphonate to give the phosphonate carbanion 1. Nucleophilic addition of the carbanion onto the aldehyde 2 (or ketone) producing 3a or 3b is the rate-limiting step. If R2 = ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Edwin Vedejs
Edwin Vedejs () ( lv, Edvīns Vedējs; January 31, 1941 – December 2, 2017) was a Latvian-American professor of chemistry. In 1967, he joined the organic chemistry faculty at University of Wisconsin. He rose through the ranks during his 32 years at Wisconsin being named Helfaer Professor (1991–1996) and Robert M. Bock Professor (1997–1998). In 1999, he moved to the University of Michigan and served as the Moses Gomberg Collegiate Professor of Chemistry for the final 13 years of his tenure. He was elected a fellow of the American Chemical Society in 2011. After his retirement in 2011, the University of Michigan established the Edwin Vedejs Collegiate Professor of Chemistry Chair. Vedejs died on December 2, 2017, in Madison, Wisconsin. Early life and education Edwin "Ed" Vedejs was born in Riga, Latvia to Velta (nee Robežnieks) and Nikolajs Vedejs. Not long after his birth, the German occupation of Latvia during World War II occurred followed by the Soviet re-occupation of Lat ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Seyferth–Gilbert Homologation
The Seyferth–Gilbert homologation is a chemical reaction of an aryl ketone 1 (or aldehyde) with dimethyl (diazomethyl)phosphonate 2 and potassium tert-butoxide to give substituted alkynes 3. Dimethyl (diazomethyl)phosphonate 2 is often called the Seyferth–Gilbert reagent. This reaction is called a ''homologation'' because the product has exactly one additional carbon more than the starting material. Reaction mechanism Deprotonation of the Seyferth–Gilbert reagent A gives an anion B, which reacts with the ketone to form the oxaphosphetane D. Elimination of dimethylphosphate E gives the vinyl diazo-intermediate Fa and Fb. The generation of nitrogen gas gives a vinyl carbene G, which via a 1,2-migration forms the desired alkyne H. Bestmann modification The dimethyl (diazomethyl)phosphonate carbanion can be generated ''in situ'' from dimethyl-1-diazo-2-oxopropylphosphonate (also called the Ohira-Bestmann reagent) by reaction with methanol and potassium carbonate as the b ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ball-and-stick Model
In chemistry, the ball-and-stick model is a molecular model of a chemical substance which displays both the three-dimensional position of the atoms and the bonds between them. The atoms are typically represented by spheres, connected by rods which represent the bonds. Double and triple bonds are usually represented by two or three curved rods, respectively, or alternately by correctly positioned sticks for the sigma and pi bonds. In a good model, the angles between the rods should be the same as the angles between the bonds, and the distances between the centers of the spheres should be proportional to the distances between the corresponding atomic nuclei. The chemical element of each atom is often indicated by the sphere's color. In a ball-and-stick model, the radius of the spheres is usually much smaller than the rod lengths, in order to provide a clearer view of the atoms and bonds throughout the model. As a consequence, the model does not provide a clear insight about th ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Molecule
A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and biochemistry, the distinction from ions is dropped and ''molecule'' is often used when referring to polyatomic ions. A molecule may be homonuclear, that is, it consists of atoms of one chemical element, e.g. two atoms in the oxygen molecule (O2); or it may be heteronuclear, a chemical compound composed of more than one element, e.g. water (two hydrogen atoms and one oxygen atom; H2O). In the kinetic theory of gases, the term ''molecule'' is often used for any gaseous particle regardless of its composition. This relaxes the requirement that a molecule contains two or more atoms, since the noble gases are individual atoms. Atoms and complexes connected by non-covalent interactions, such as hydrogen bonds or ionic bonds, are typically not consid ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phosphorus
Phosphorus is a chemical element with the symbol P and atomic number 15. Elemental phosphorus exists in two major forms, white phosphorus and red phosphorus, but because it is highly reactive, phosphorus is never found as a free element on Earth. It has a concentration in the Earth's crust of about one gram per kilogram (compare copper at about 0.06 grams). In minerals, phosphorus generally occurs as phosphate. Elemental phosphorus was first isolated as white phosphorus in 1669. White phosphorus emits a faint glow when exposed to oxygen – hence the name, taken from Greek mythology, meaning 'light-bearer' (Latin ), referring to the " Morning Star", the planet Venus. The term '' phosphorescence'', meaning glow after illumination, derives from this property of phosphorus, although the word has since been used for a different physical process that produces a glow. The glow of phosphorus is caused by oxidation of the white (but not red) phosphorus — a process now called chem ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Oxygen
Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as well as with other compounds. Oxygen is Earth's most abundant element, and after hydrogen and helium, it is the third-most abundant element in the universe. At standard temperature and pressure, two atoms of the element bind to form dioxygen, a colorless and odorless diatomic gas with the formula . Diatomic oxygen gas currently constitutes 20.95% of the Earth's atmosphere, though this has changed considerably over long periods of time. Oxygen makes up almost half of the Earth's crust in the form of oxides.Atkins, P.; Jones, L.; Laverman, L. (2016).''Chemical Principles'', 7th edition. Freeman. Many major classes of organic molecules in living organisms contain oxygen atoms, such as proteins, nucleic acids, carbohydrates, and fats, as ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with other atoms when it forms chemical compounds or molecules. Description The combining capacity, or affinity of an ...—its atom making four electrons available to form covalent bond, covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes up only about 0.025 percent of Earth's crust. Three Isotopes of carbon, isotopes occur naturally, Carbon-12, C and Carbon-13, C being stable, while Carbon-14, C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the Timeline of chemical element discoveries#Ancient discoveries, few elements known since antiquity. Carbon is the 15th Abundance of elements in Earth's crust, most abundant element in the Earth's crust, and the Abundance of the c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chemical Society Reviews
''Chemical Society Reviews'' is a biweekly peer-reviewed scientific journal published by the Royal Society of Chemistry, for review articles on topics of current interest in chemistry. Its predecessors were ''Quarterly Reviews, Chemical Society'' (1947–1971) and ''Royal Institute of Chemistry, Reviews'' (1968–1971); it maintained its current title since 1971. According to the ''Journal Citation Reports'', the journal has a 2020 impact factor of 54.564. The current editor-in-chief (Chair of Editorial Board) is Douglas Stephan. ''Chemical Society Reviews'' publishes occasional themed issues on new and emerging areas of research in the chemical sciences. These issues are edited by a guest editor who is a specialist in their field. Since 2005, ''Chemical Society Reviews'' has published reviews on topics of broad appeal, termed "social interest" reviews, such as articles on art conservation, forensics, and automotive fuels. The journal is abstracted and indexed in PubMed/MEDLINE ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nuclear Magnetic Resonance Spectroscopy
Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy or magnetic resonance spectroscopy (MRS), is a spectroscopic technique to observe local magnetic fields around atomic nuclei. The sample is placed in a magnetic field and the NMR signal is produced by excitation of the nuclei sample with radio waves into nuclear magnetic resonance, which is detected with sensitive radio receivers. The intramolecular magnetic field around an atom in a molecule changes the resonance frequency, thus giving access to details of the electronic structure of a molecule and its individual functional groups. As the fields are unique or highly characteristic to individual compounds, in modern organic chemistry practice, NMR spectroscopy is the definitive method to identify monomolecular organic compounds. The principle of NMR usually involves three sequential steps: # The alignment (polarization) of the magnetic nuclear spins in an applied, constant magnetic field B0. # The ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
