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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 ...
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 ...
The mechanism of homogeneous ring-opening metathesis polymerization is well-studied. It is similar to any olefin metathesis reaction. Initiation occurs by forming an open coordination site on the catalyst. Propagation happens via a metallacycle intermediate formed after a 2+2 cycloaddition. When using a G3 catalyst, 2+2 cycloaddition is the ...
The mechanism for transition metal-catalyzed olefin metathesis has been widely researched over the past forty years. [20] RCM undergoes a similar mechanistic pathway as other olefin metathesis reactions, such as cross metathesis (CM), ring-opening metathesis polymerization (ROMP), and acyclic diene metathesis (ADMET). [21]
In the 1960s, ruthenium trichloride was found to catalyze olefin metathesis. Processes were commercialized based on these discoveries. These ill-defined but highly active homogeneous catalysts remain in industrial use. [6] The first well-defined ruthenium catalyst was reported in 1992. [7] It was prepared from RuCl 2 (PPh 3) 4 and ...
Olefin metathesis is a formal exchange of the alkylidene fragments in two alkenes. It is a catalytic reaction with carbene, or more accurately, transition metal carbene complex intermediates. In this example (ethenolysis, a pair of vinyl compounds form a new symmetrical alkene with expulsion of ethylene.
The 2-butenes are then subjected to metathesis with ethylene. Rhenium- and molybdenum-containing heterogeneous catalysis are used. Nowadays, only the "reverse" reaction is practiced, i.e., the conversion of ethylene and 2-butene to propylene: [2] CH 2 =CH 2 + CH 3 CH=CHCH 3 → 2 CH 2 =CHCH 3
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.