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In organic chemistry, olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. [ 1 ] [ 2 ] Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative ...
In 1974 Schrock discovered the alpha hydrogen abstraction reaction, which creates alkylidene complexes from alkyls and alkylidyne complexes from alkylidenes. At MIT Schrock was the first to elucidate the structure and mechanism of so-called 'black box' olefin metathesis catalysts.
The metal-mediated processes include a carbonyl-olefination and an olefin–olefin metathesis event. There are two general mechanistic schemes to perform this overall transformation: one, reaction of a [M=CHR 1] reagent with an alkene to generate a new metal alkylidene, which then couples with a carbonyl group to form the desired substituted alkene and an inactive [M=O] species (type A); two ...
Grubbs was instrumental in developing a family of ruthenium catalysts, including Grubbs catalyst for olefin metathesis. [36] He studied olefin transformations for ring-closing metathesis (RCM), [37] cross-metathesis reaction (CMR), [38] and ring-opening metathesis polymerization (ROMP) with cyclic olefins such as norbornene. [39] He also ...
Ring-closing metathesis (RCM) is a widely used variation of olefin metathesis in organic chemistry for the synthesis of various unsaturated rings via the intramolecular metathesis of two terminal alkenes, which forms the cycloalkene as the E-or Z-isomers and volatile ethylene. [1] [2]
Corey-Seebach reaction; Corey–Winter olefin synthesis; Corey–Winter reaction; Cornforth rearrangement; Coupling reaction; Crabbé reaction; Craig method; Cram's rule of asymmetric induction; Creighton process; Criegee reaction; Criegee rearrangement; Cross metathesis; Crum Brown–Gibson rule; Curtius degradation; Curtius rearrangement ...
Besides olefin metathesis (described above), many pericyclic reactions can be used such as the ene reaction and the Cope rearrangement. Cope rearrangement of divinylcyclobutane to cyclooctadiene In the Diels–Alder reaction , a cyclohexene derivative is prepared from a diene and a reactive or electron-deficient alkene.
Grubbs catalysts are of interest for olefin metathesis. [25] [26] It is mainly applied to fine chemical synthesis. Large-scale commercial applications of olefin metathesis almost always employ heterogeneous catalysts or ill-defined systems based on ruthenium trichloride. [6]