Decarbonylation

Many organic carbonyls undergo decarbonylation. A common transformation involves the conversion of aldehydes to alkanes, usually catalyzed by metal complexes:^[1]

RCHO → RH + CO

Usually decarbonylation is undesirable because a functional group is lost. These reactions proceed via metal acyl hydrides. Ketones and other carbonyl-containing functional groups are more resistant to decarbonylation than are aldehydes.

The reverse reaction, the insertion of CO into a bond, is also a common and industrially relevant reaction. Decarbonylations are often in competition with the reverse carbonylation reaction.

Decarbonylation of Dimethyl oxalate to Dimethyl carbonate

References

1. ↑ Hartwig, J. F. Organotransition Metal Chemistry, from Bonding to Catalysis; University Science Books: New York, 2010.