Olefin Metathesis

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

概述

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.

日常示例

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

工业重要性

烯烃复分解是合成精细化学品、药物中间体及高分子材料的核心反应之一，广泛应用于工业生产。

属性

类型
Organic
可逆
是
能量
放热
ΔH
-5.0 kJ/mol
催化剂
Grubbs catalyst (Ru-based)

相关反应

Swern Oxidation Oxidation of Secondary Alcohol to Ketone Claisen Condensation (Ethyl Acetate) Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Catalytic Hydrogenation of Ethylene Condensation Polymerization (Nylon 6,6) Cope Rearrangement Epoxidation of Alkenes (mCPBA)

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)).