Olefin Metathesis

2 R–CH=CH–R' ⇌ R–CH=CH–R + R'–CH=CH–R'

Visão geral

Olefin metathesis exchanges substituents around carbon-carbon double bonds using a ruthenium or molybdenum carbene catalyst. The mechanism involves [2+2] cycloaddition to form a metallacyclobutane, followed by cycloreversion. Chauvin, Grubbs, and Schrock shared the 2005 Nobel Prize for this reaction.

Exemplo do cotidiano

Ring-closing metathesis is used to produce macrocyclic drug molecules like the hepatitis C drug simeprevir.

Importância industrial

O processo SHOP da Shell utiliza metátese cruzada para produzir alfa-olefinas para detergentes. A metátese está a transformar a síntese farmacêutica.

Propriedades

Tipo: Organic
Reversível: Sim
Energia: Exotérmico
ΔH: -5,0 kJ/mol
Catalisador: Grubbs catalyst (Ru-based)

Reações relacionadas

Epoxidation of Alkenes (mCPBA) Swern Oxidation Oxidation of Secondary Alcohol to Ketone E2 Elimination (Dehydrohalogenation) Claisen Condensation (Ethyl Acetate) Aldol Condensation of Acetaldehyde Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Dehydration of Ethanol

Frequently Asked Questions

What is the equation for Olefin Metathesis?

The balanced equation is: 2 R–CH=CH–R' ⇌ R–CH=CH–R + R'–CH=CH–R'.

What type of reaction is Olefin Metathesis?

Olefin Metathesis is a organic reaction. It is reversible under certain conditions.

Is Olefin Metathesis exothermic or endothermic?

Olefin Metathesis is exothermic (releases energy). The enthalpy change (ΔH) is -5.0 kJ/mol.

What conditions are needed for Olefin Metathesis?

This reaction requires a catalyst (Grubbs catalyst (Ru-based)).