Staudinger Reaction
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Staudinger Reaction
The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered by and named after Hermann Staudinger. The reaction follows this stoichiometry: :R3P + R'N3 → R3P=NR' + N2 Staudinger reduction The Staudinger reduction is conducted in two steps. First phosphine imine-forming reaction is conducted involving treatment of the azide with the phosphine. The intermediate, e.g. triphenylphosphine phenylimide, is then subjected to hydrolysis to produce a phosphine oxide and an amine: :R3P=NR' + H2O → R3P=O + R'NH2 The overall conversion is a mild method of reducing an azide to an amine. Triphenylphosphine or tributylphosphine are most commonly used, yielding tributylphosphine oxide or triphenylphosphine oxide as a side product in addition to the desired amine. An example of a Staudinger reduction is the organic synthesis of the pinwheel compound 1,3,5-tris(aminomethyl)-2,4,6-triethylbenz ...
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Hermann Staudinger
Hermann Staudinger (; 23 March 1881 – 8 September 1965) was a German organic chemist who demonstrated the existence of macromolecules, which he characterized as polymers. For this work he received the 1953 Nobel Prize in Chemistry. He is also known for his discovery of ketenes and of the Staudinger reaction. Staudinger, together with Leopold Ružička, also elucidated the molecular structures of pyrethrin I and II in the 1920s, enabling the development of pyrethroid insecticides in the 1960s and 1970s. Early work Staudinger was born in 1881 in Worms. Staudinger, who initially wanted to become a botanist, studied chemistry at the University of Halle, at the TH Darmstadt and at the LMU Munich. He received his "Verbandsexamen" (comparable to Master's degree) from TH Darmstadt. After receiving his Ph.D. from the University of Halle in 1903, Staudinger qualified as an academic lecturer at the University of Strasbourg in 1907. It was here that he discovered the ketenes, a family ...
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Tributylphosphine
Tributylphosphine is the organophosphorus compound with the formula P(CH). Abbreviated or PBu, it is a tertiary phosphine. It is an oily liquid at room temperature, with a nauseating odor. It reacts slowly with atmospheric oxygen, and rapidly with other oxidizing agents, to give the corresponding phosphine oxide. It is usually handled using air-free techniques. Preparation Tributylphosphine is prepared industrially by the hydrophosphination of phosphine with butene: the addition proceeds by a free radical mechanism, and so the Markovnikov rule is not followed. :PH + 3CH=CHCHCH → P(CHCHCHCH) Tributylphosphine can be prepared in the laboratory by reaction of the appropriate Grignard reagent with phosphorus trichloride although, as it is commercially available at reasonable prices, it is rare to have to perform the small-scale preparation. :3 BuMgCl + PCl → PBu + 3 MgCl Reactions Tributylphosphine reacts with oxygen to give the phosphine oxide: :2 PBu3 + O2 → 2 OPBu3 Because ...
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Organic Redox Reactions
Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product of decay, or is composed of organic compounds * Organic compound, a compound that contains carbon ** Organic chemistry, chemistry involving organic compounds Farming, certification and products * Organic farming, agriculture conducted according to certain standards, especially the use of stated methods of fertilization and pest control * Organic certification, accreditation process for producers of organically-farmed products * Organic horticulture, the science and art of growing fruits, vegetables, flowers, or ornamental plants by following the essential principles of organic agriculture * Organic products, "organics": ** Organic food, food produced from organic farming methods and often certified organic according to organic farming stand ...
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Traceless StaudingerLigation
In linear algebra, the trace of a square matrix , denoted , is defined to be the sum of elements on the main diagonal (from the upper left to the lower right) of . The trace is only defined for a square matrix (). It can be proved that the trace of a matrix is the sum of its (complex) eigenvalues (counted with multiplicities). It can also be proved that for any two matrices and . This implies that similar matrices have the same trace. As a consequence one can define the trace of a linear operator mapping a finite-dimensional vector space into itself, since all matrices describing such an operator with respect to a basis are similar. The trace is related to the derivative of the determinant (see Jacobi's formula). Definition The trace of an square matrix is defined as \operatorname(\mathbf) = \sum_^n a_ = a_ + a_ + \dots + a_ where denotes the entry on the th row and th column of . The entries of can be real numbers or (more generally) complex numbers. The trace is not ...
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Chemical Biology
Chemical biology is a scientific discipline spanning the fields of chemistry and biology. The discipline involves the application of chemical techniques, analysis, and often small molecules produced through synthetic chemistry, to the study and manipulation of biological systems. In contrast to biochemistry, which involves the study of the chemistry of biomolecules and regulation of biochemical pathways within and between cells, chemical biology deals with chemistry ''applied to'' biology (synthesis of biomolecules, the simulation of biological systems, etc.). Introduction Some forms of chemical biology attempt to answer biological questions by studying biological systems at the chemical level. In contrast to research using biochemistry, genetics, or molecular biology, where mutagenesis can provide a new version of the organism, cell, or biomolecule of interest, chemical biology probes systems ''in vitro'' and ''in vivo'' with small molecules that have been designed for a specific ...
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Staudinger Mechanism2
Staudinger is a German surname. Notable people with the surname include: *Alma Staudinger (1921–2017), Austrian diver *Christian W. Staudinger (born 1952), German artist *Christina Staudinger (born 1987), Austrian freestyle skier *Conny Staudinger (born 1927), Austrian ice hockey player *Hannes Staudinger (1907–1974), Austrian cinematographer * Hans Staudinger (1889–1980), German politician *Hermann Staudinger (1881–1965), German chemist who demonstrated the existence of macromolecules and was the winner of the 1953 Nobel Prize in Chemistry *Josef Staudinger (1906–1998), Austrian diver who competed in the 1928 and 1932 Summer Olympics *Magda Staudinger (1902–1997), Latvian biologist and botanist *Magdalene Epply-Staudinger (1907–2005), Austrian diver *Otto Staudinger (1830–1900), German entomologist *Rupert Staudinger (born 1997), British-German luger *Stella Staudinger (born 1972), Austrian basketball player *Ursula Staudinger (born 1959), German psychologist *Wolfga ...
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Nitrogen
Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at seventh in total abundance in the Milky Way and the Solar System. At standard temperature and pressure, two atoms of the element bond to form N2, a colorless and odorless diatomic gas. N2 forms about 78% of Earth's atmosphere, making it the most abundant uncombined element. Nitrogen occurs in all organisms, primarily in amino acids (and thus proteins), in the nucleic acids ( DNA and RNA) and in the energy transfer molecule adenosine triphosphate. The human body contains about 3% nitrogen by mass, the fourth most abundant element in the body after oxygen, carbon, and hydrogen. The nitrogen cycle describes the movement of the element from the air, into the biosphere and organic compounds, then back into the atmosphere. Many indus ...
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Diatomic
Diatomic molecules () are molecules composed of only two atoms, of the same or different chemical elements. If a diatomic molecule consists of two atoms of the same element, such as hydrogen () or oxygen (), then it is said to be homonuclear. Otherwise, if a diatomic molecule consists of two different atoms, such as carbon monoxide () or nitric oxide (), the molecule is said to be heteronuclear. The bond in a homonuclear diatomic molecule is non-polar. The only chemical elements that form stable homonuclear diatomic molecules at standard temperature and pressure (STP) (or typical laboratory conditions of 1 bar and 25 °C) are the gases hydrogen (), nitrogen (), oxygen (), fluorine (), and chlorine (). The noble gases (helium, neon, argon, krypton, xenon, and radon) are also gases at STP, but they are monatomic. The homonuclear diatomic gases and noble gases together are called "elemental gases" or "molecular gases", to distinguish them from other gases that are chemical ...
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Nucleophilic Addition
In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic additions differ from electrophilic additions in that the former reactions involve the group to which atoms are added accepting electron pairs, whereas the latter reactions involve the group donating electron pairs. Addition to carbon–heteroatom double bonds Nucleophilic addition reactions of nucleophiles with electrophilic double or triple bond (π bonds) create a new carbon center with two additional single, or σ, bonds.March Jerry; (1985). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc. Addition of a nucleophile to carbon–heteroatom double or triple bonds such as >C=O or -C≡N show great variety. These types of bonds are polar (have a large difference in electronegativity betwe ...
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Reaction Mechanism
In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs. A chemical mechanism is a theoretical conjecture that tries to describe in detail what takes place at each stage of an overall chemical reaction. The detailed steps of a reaction are not observable in most cases. The conjectured mechanism is chosen because it is thermodynamically feasible, and has experimental support in isolated intermediates (see next section) or other quantitative and qualitative characteristics of the reaction. It also describes each reactive intermediate, activated complex, and transition state, and which bonds are broken (and in what order), and which bonds are formed (and in what order). A complete mechanism must also explain the reason for the reactants and catalyst used, the stereochemistry observed in reactants and products, all products formed and the amount of each. The electron or arrow pushing method is often used in i ...
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Organic Synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one of the most important branches of organic chemistry. There are several main areas of research within the general area of organic synthesis: ''total synthesis'', ''semisynthesis'', and ''methodology''. Total synthesis A total synthesis is the complete chemical synthesis of complex organic molecules from simple, commercially available petrochemical or natural precursors. Total synthesis may be accomplished either via a linear or convergent approach. In a ''linear'' synthesis—often adequate for simple structures—several steps are performed one after another until the molecule is complete; the chemical compounds made in each step are called synthetic intermediates. Most often, each step in a synthesis refers to a separate rea ...
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