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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 reaction is an example of cross metathesis. The utility of the reaction is driven by the low cost of ethylene as a reagent and its selectivity. It produces compounds with terminal alkene functional groups (α-olefins), which are more amenable to other reactions such as polymerization and hydroformylation. The general reaction equation is:
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 Shell higher olefin process (SHOP) is a chemical process for the production of linear alpha olefins via ethylene oligomerization and olefin metathesis invented and exploited by Shell plc. [1] The olefin products are converted to fatty aldehydes and then to fatty alcohols , which are precursors to plasticizers and detergents .
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]
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.
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 ...
Factors governing organic reactions are essentially the same as that of any chemical reaction.Factors specific to organic reactions are those that determine the stability of reactants and products such as conjugation, hyperconjugation and aromaticity and the presence and stability of reactive intermediates such as free radicals, carbocations and carbanions.