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

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)).