Olefin Metathesis

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

ภาพรวม

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.

ตัวอย่างในชีวิตประจำวัน

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

ความสำคัญทางอุตสาหกรรม

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

คุณสมบัติ

ประเภท: Organic
ย้อนกลับได้: ใช่
พลังงาน: คายความร้อน
ΔH: -5.0 kJ/mol
ตัวเร่งปฏิกิริยา: Grubbs catalyst (Ru-based)

ปฏิกิริยาที่เกี่ยวข้อง

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)).