Olefin Metathesis

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

概要

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.

日常の例

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

産業上の重要性

Shellの SHOP プロセスはクロスメタセシスにより洗剤用α-オレフィンを製造する。メタセシスは医薬品合成を大きく変革している。

特性

タイプ
Organic
可逆的
はい
エネルギー
発熱性
ΔH
-5.0 kJ/mol
触媒
Grubbs catalyst (Ru-based)

関連する反応

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)).