Research Review By:
Conley, Matthew P. Department of Chemistry, Eidgenössische Technische Hochschule (ETH) Zürich, Zürich, Switzerland.
Copéret, Christophe Department of Chemistry, Eidgenössische Technische Hochschule (ETH) Zürich, Zürich, Switzerland.
- Tandem alkane metathesis
- Single-component alkane metathesis
- Links to Primary Literature
Alkane metathesis is a reaction that transforms an alkane (CnH2n+2) or an alkane mixture into lower and higher homologues. An example of alkane metathesis is the ideal reaction of propane, which would yield butane and ethane [the (n+1) and (n−1) homologues]; however, in practice, higher and lower homologues (hexanes, pentanes, and methane) are also formed [reactions (1)]. These reactions are typically thermoneutral [the change in the Gibbs energy (ΔG) is close to 0] and require a catalyst or a mixture of catalysts. While reaction (1b) is formally analogous to alkene and alkyne metathesis, where alkylidene (R2CM) and alkylidyne (RCM) groups are exchanged at a transition-metal center upon reaction with alkene and alkyne mixtures, the redistribution of alkyl fragments does not take place by cleavage of carbon-carbon sigma (σ) bonds with a metal-carbon σ-bond (σ-bond metathesis mechanisms), but rather involves alkylidene and alkene intermediates. The detailed mechanism depends on the catalyst system, which can be divided into two families: tandem systems involving two catalysts and single-component catalysts. Overall, tandem and single-component alkane metatheses are promising reactions that could enable the upgrading of hydrocarbons, in particular, converting natural-gas resources into valuable liquid fuels.
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