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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