Olefin Metathesis

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

Tổng quan

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.

Ví dụ thực tế

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

Tầm quan trọng công nghiệp

Shell's SHOP process uses cross-metathesis to produce alpha-olefins for detergents. Metathesis is transforming pharmaceutical synthesis.

Tính chất

Loại: Organic
Thuận nghịch: Có
Năng lượng: Tỏa nhiệt
ΔH: -5,0 kJ/mol
Chất xúc tác: Grubbs catalyst (Ru-based)

Phản ứng liên quan

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)).