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

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)).