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Metathesis Reaction

Metathesis reaction involves the exchange of atoms or functional groups between substrates to form new compounds, commonly occurring in olefin metathesis. This process can be categorized into cross metathesis, ring-closing metathesis, and ring-opening metathesis polymerization, each with distinct mechanisms and applications. Notable chemists Yves Chauvin, Richard R. Schrock, and Robert H. Grubbs contributed to the development of olefin metathesis, which utilizes transition metal-based carbene catalysts.

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20 views

Metathesis Reaction

Metathesis reaction involves the exchange of atoms or functional groups between substrates to form new compounds, commonly occurring in olefin metathesis. This process can be categorized into cross metathesis, ring-closing metathesis, and ring-opening metathesis polymerization, each with distinct mechanisms and applications. Notable chemists Yves Chauvin, Richard R. Schrock, and Robert H. Grubbs contributed to the development of olefin metathesis, which utilizes transition metal-based carbene catalysts.

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mahezwizard321
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Metathesis Reaction

Metathesis reaction is the exchange of atoms or functional groups in substrates and


the rearrangement of their matching partners (substituents) to form new
compounds. Also known as exchange reaction, metathesis is a bimolecular process
resulting in products with similar bonding.

Types and Examples of Metathesis Reaction

Olefin (Alkene) Metathesis

Olefin metathesis is a commonly occurring metathesis reaction that takes


place between two alkenes. It is widely popular for the synthesis of
unsaturated olefinic compounds and their polymeric counterparts. This
type of metathesis reaction occurs when two olefin substrates form a four-
membered ring intermediate and then rearrange the substituents to form
two new carbon-carbon double bonds. The transfer of substituents
between the different olefins is also known as transalkylidenation. Olefin
metathesis is carried out in the presence of a transition metal-based
carbene catalyst.

French chemist Yves Chauvin and American chemists Richard R. Schrock


and Robert H. Grubbs developed the olefin metathesis reaction.

Types of Olefin Metathesis

1.1 Cross Metathesis

Cross metathesis is the transalkylidenation of two different alkenes


resulting in a trans-alkene. Cross metathesis can occur both in the
terminal and non-terminal alkenes. Homocoupling of pairs may also result.

General Reaction for Cross Metathesis in Non-terminal Alkene

R1CH = CHR2 + R3CH = CHR4 ⇋ R1CH = CHR3 + R2CH = CHR4

Example: A reversible reaction between ethene (C2H4) and 2-butene


(C4H8) breaks the carbon-carbon double bonds and then rearranges to
form propene (C3H6).

H3C-CH=CH-CH3 + H2C=CH2 ⇋ 2 H3C-CH=CH2

General Reaction for Cross Metathesis in Terminal Alkenes


R1-CH=CH2 + H2C=CH-R2 ⇋ R1-CH=CH-R2 + H2C=CH2
Example: 1-butene (C4H8) undergoes a reversible reaction with propene (C 3H6) to

give 2-pentene (C5H10) and ethene (C2H4).


H3C-CH2-CH=CH2 + H2C=CH-CH3 ⇋ H3C-CH2-CH=CH-CH3 + H2C=CH2
1.2 Ring-closing Metathesis (RCM)

Ring-closing metathesis (RCM) is a variation of olefin metathesis to synthesize


various unsaturated rings via the intramolecular metathesis of two terminal alkenes
or a diene. The final products are cycloalkene (E- or Z- isomer) and volatile ethylene.
Example: 4-methyl-1,7-octadiene undergoes RCM to form 4-methylcyclohexene.

1.3 Ring-opening Metathesis Polymerization (ROMP)


Ring-opening metathesis polymerization is a chain polymerization reaction carried
out by the metathesis process. This reaction is thermodynamically favored for a
strained-ring system and can be opened by a ruthenium-carbene catalyst. A second
alkene is produced through cross metathesis.
Example: Norbornene is polymerized by ROMP to get polynorbornene.

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