Olefin Metathesis

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

개요

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.

일상 속 예시

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

산업적 중요성

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성질

유형
Organic
가역 반응
예
에너지
발열
ΔH
-5.0 kJ/mol
촉매
Grubbs catalyst (Ru-based)

관련 반응

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)).